Herbicidal thiadiazabicyclooctanes

ABSTRACT

Thiadiazabicyclooctanes of formula I ##STR1## wherein Z is oxygen or sulfur; 
     R 53  is hydrogen or C 1  -C 6  alkyl; 
     R 54  is C 1  -C 6  alkyl, C 1  -C 6  alkoxy, C 3  -C 6  alkenyloxy, C3-C6alkynyioxy, hydroxy or C 1  -C 6  haloalkoxy; or 
     R 53  and R 54 , together with the carbon atom to which they are bonded, form an unsubstituted 3-, 4-, 5- or 6-membered saturated ring; 
     W is a group of formulae W 1  to W 10  ##STR2##

The present invention relates to novel, herbicidally active thiadiazabicyclooctanes, to processes for the preparation thereof, to compositions comprising those compounds as active ingredients, and to the use thereof in the control of weeds, especially selectively in crops of useful plants, such as cereals, maize, soybeans, rape, rice and cotton.

Thiadiazabicyclo derivatives having herbicidal action are already known. Such compounds are disclosed, for example, in EP-A-0 238 711, EP-A-0 304 920, U.S. Pat. No. 4,885,023, U.S. Pat. No. 4,684,397 and U.S. Pat. No. 4,801,408.

Novel thiadiazabicyclooctanes having selective herbicidal action have now been found.

The thiadiazabicyclooctanes according to the invention have the formula ##STR3## wherein Z is oxygen or sulfur;

R₅₃ is hydrogen or C₁ -C₆ alkyl;

R₅₄ is C₁ -C₆ alkyl, C₁ -C₆ alkoxy, C₃ -C₆ alkenyloxy, C₃ -C₆ alkynyloxy, hydroxy or C₁ -C₆ haloalkoxy; or

R₅₃ and R₅₄, together with the carbon atom to which they are bonded, form an unsubstituted 3-,4-, 5- or 6-membered saturated ring;

W is a group of formulae W₁ to W₁₀ ##STR4## wherein R₁, R₂₂, R₂₃, R₂₄, R₂₇, R₃₀, R₃₃, R₃₇, R₃₈ and R₄₁ are each independently of the others hydrogen or halogen;

R₂ is hydrogen, cyano, nitro, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkoxy or C₁ -C₄ haloalkyl; is hydrogen, cyano, nitro, ##STR5## A₁ is cyano or --COR₁₆ ; R₃ is halogen, --X₄ -R₅, amino, C₁ -C₄ alkylamino, di-C₁ -C₄ alkylamino, C₂ -C₄ haloalkylamino, di-C₂ -C₄ haloalkylamino, C₁ -C₄ alkoxyalkylamino, di-C₁ -C₄ alkoxyalkylamino, C₃ - or C₄ -alkenylamino, diallylamino, -N-pyrrolidino, -N-piperidino, -N-morpholino,-N-thiomorpholino,-N-piperazino, --O--N═C(CH₃)--CH₃ or --O--CH₂ --CH₂ --O--N═C(CH₃)--CH₃ ;

R₄, R₄₂ and R₄₃ are each independently of the others hydrogen, C₁ -C₁₀ alkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, C₁ -C₈ haloalkyl, C₂ -C₈ alkenyl, C₂ -C₈ haloalkenyl, C₃ -C₈ alkynyl, C₃ -C₇ cycloalkyl, halo-C₃ -C₇ cycloalkyl, C₁ -C₈ alkylcarbonyl, allylcarbonyl, C₃ -C₇ cycloalkylcarbonyl, benzoyl that is unsubstituted or is substituted at the phenyl ring by one to three identical or different substituents selected from halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy and C1-C₄ alkoxy; C₁ -C₆ alkyl substituted by cyano, nitro, carboxy, C₁ -C₈ alkylthio-C₁ -C₈ alkoxycarbonyl, phenyl, halophenyl, C₁ -C₄ alkylphenyl, C₁ -C₄ alkoxyphenyl, C₁ -C₄ haloalkylphenyl, C₁ -C₄ haloalkoxyphenyl, C₁ -C₆ alkoxycarbonyl, C₁ -C₄ alkoxy-C₁ -C₈ alkoxycarbonyl, C₃ -C₈ alkenyloxycarbonyl, C₃ -C₈ alkynyloxycarbonyl, C.sub. 1 -C₈ alkylthiocarbonyl, C₃ -C₈ alkenylthiocarbonyl, C₃ -C₈ alkynylthiocarbonyl, carbamoyl, C₁ -C₄ alkylaminocarbonyl, di-C₁ -C₄ alkylaminocarbonyl; phenylaminocarbonyl that is unsubstituted or is substituted at the phenyl by one to three identical or different substituents selected from halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy and C₁ -C₄ alkoxy or by one substituent selected from cyano and nitro; dioxolan-2-yl that is unsubstituted or substituted by one or two C₁ -C₄ alkyl radicals; or dioxanyl that is unsubstituted or substituted by one or two C₁ -C₄ alkyl radicals;

R₅ is hydrogen, C₁ -C₁₀ alkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₂ -C₈ haloalkyl, C₁ -C₁₀ alkyl-thio-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, cyano-C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ haloalkenyl, C₃ -C₈ alkynyl, C₃ -C₇ cycloalkyl, C₃ -C₇ cycloalkyl-C₁ -C₄ alkyl, halo-C₃ -C₇ cycloalkyl, or benzyl that is unsubstituted or is substituted at the phenyl ring by one to three identical or different substituents selected from halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy and C₁ -C₄ alkoxy; or is an alkali metal, an alkaline earth metal or an ammonium ion; or is the group --[CHR₆ (CH₂)_(n4) ]--COOR₇ ;

R₆, R₂₀, R₂₁, R₂₆, R₂₈, R₃₂, R₃₄, R₃₉, R₄₀, R₄₆ R₄₇, R₄₉, R₅₀, R₅₁ and R₅₂ are each independently of the others hydrogen or C₁ -C₄ alkyl;

R₇ and R₄₈ are each independently of the other hydrogen, C₁ -C₆ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ alkoxy-C₂ -C₁ -₈ alkyl, C₁ -C₈ alkylthio-C₁ -C₈ alkyl or C₃ -C₇ cycloalkyl;

R₈ is hydrogen or C₁ -C₄ alkyl;

R₄₄ and R₄₅ are each independently of the other hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or C₁ -C₄ alkoxy-C₁ -C₄ alkyl;

R₉ and R₁₀ are each independently of the other C₁ -C₄ alkyl, C₂ -C₄ haloalkyl or C₂ -C₈ alkoxyalkyl; or

R₉ and R₁₀ together are an ethano-, a propano- or a cyclohexane-1,2-diyl bridge, those groups either being unsubstituted or being substituted by one or two radicals selected from the group C₁ -C₄ alkyl, C₁ -C₄ haloalkyl and C₁ -C₄ -hydroxyalkyl;

R₁₁ is hydrogen, C₁ -C₅ alkyl or C₃ -C₇ alkenyl;

R₁₂ is C₁ -C₈ alkyl;

R₁₃ is hydrogen, C₁ -C₅ alkyl, benzyl, C₁ -C₄ haloalkyl, C₃ -C₈ alkenyl or C₃ -C₈ alkynyl;

R₁₄ is C₁ -C₆ alkyl, C₁ -C₅ haloalkyl or di-C₁ -C₄ alkylamino;

R₁₅ is hydrogen, fluorine, chlorine, bromine, C₁ -C₄ alkyl or trifluoromethyl;

R₁₆ is chlorine,--X₅ --R₁₇, amino, C₁ -C₄ alkylamino, di-C₁ -C₄ alkylamino, C₂ -C₄ haloalkylamino, di-C₂ -C₄ haloalkylamino, C₁ -C₄ alkoxyalkylamino, di-C₁ -C₄ alkoxyalkylamino, C₃ -C₄ alkenylamino, diallylamino,-N-pyrrolidino,-N-piperidino, -N-morpholino, -N-thiomorpholino, -N-piperazino, or the group --O--N═C(CH₃)--CH₃, --O--CH₂ --CH₂ --O--N═C(CH₃)--CH₃ or-N(OR₄₆)--R₆ ;

R₁₇ is hydrogen, C₁ -C₁₀ alkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₂ -C₈ haloalkyl, C₁ -C₁₀ alkyl-thio-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, cyano-C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ haloalkenyl, C₃ -C₈ alkynyl, C₃ -C₇ cycloalkyl, C₃ -C₇ cycloalkyl-C₁ -C₄ alkyl, halo-C₃ -C₇ cycloalkyl, or benzyl that is unsubstituted or is substituted at the phenyl ring by one to three identical or different substituents selected from halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy and C₁ -C₄ alkoxy; or is an alkali metal, an alkaline earth metal or an ammonium ion, or is the group --[CHR₄₇ --(CH₂)_(m) ]--COOR₄₈ or --[CHR₄₉ --(CH₂)_(t) --Si(R₁₈)₃ ];

m is 0, 1, 2, 3 or 4;

t is 0, 1, 2, 3 or 4;

R₁₈ is C₁ -C₄ alkyl;

R₁₉ is hydrogen, C₁ -C₆ alkyl, C₂ -C₄ alkenyl or C₂ -C₆ alkynyl; halo-substituted C₁ -C₆ alkyl, C₂ -C₄ alkenyl or C₃ -C₆ alkynyl; C₁ -C₄ aalkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkoxy-C₁ -C₂ alkoxy-C₁ -C₂ alkyl, 1-phenylpropen-3-yl, C₁ -C₆ alkyl substituted by cyano or by C₃ -C₆ cycloalkyl; carboxy-C₁ -C₄ alkyl, C₁ -C₆ alkoxycarbonyl-C₁ -C₄ alkyl, C₂ -C₆ haloalkoxycarbonyl-C₁ -C₄ alkyl, C₁ -C₄ alkoxy-C₁ -C₂ alkoxycarbonyl-C₁ -C₄ alkyl, C₁ -C₆ alkoxycarbonyl-C₁ -C₂ alkoxycarbonyl-C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl-C₁ -C₂ alkoxycarbonyl-C₁ -C₄ alkyl, C₁ -C₅ alkylaminocarbonyl-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, di-C₁ -C₅ alkylaminocarbonyl-C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, benzyl or halo-substituted benzyl, C₁ -C₈ alkylcarbonyl ##STR6## C₁ -C₄ alkylthiocarbonyl-C₁ -C₄ alkyl, or the group --[CHR₄₇ --(CH₂)_(m) ]COX₆ --CHR₄₇ --(CH₂)_(m) --COOR₄₈ ;

R₂₅, R₂₉, R₃₁, R₃₅ and R36 are each independently of the others hydrogen, C₁ -C₄ alkyl, C₁ -C₆ haloalkyl, C₃ -C₈ alkenyl, C₃ -C₈ haloalkenyl, C₃ -C₈ alkynyl, C₁ C₄ alkoxy-C₁ -C₈ alkyl, cyano-C₁ -C₄ alkyl, C₁ -C₈ alkoxycarbonyl-C₁ -C₄ alkyl, C₃ -C₇ cycloalkyl, C₃ -C₇ cycloalkyl-C₁ -C₄ alkyl, benzyl, C₁ -C₄ alkyl substituted by -N-morpholino, -N-thiomorpholino or by -N-piperazino, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, C₁ -C₄ alkylaminocarbonyl-C₁ -C₄ alkyl, di-C₁ -C₄ alkylaminocarbonyl-C₁ -C₄ alkyl, C₁ -C₄ alkoxycarbonyl or C₁ -C₄ alkylcarbonyl;

X₁, X₂, X₃, X₄, X₅ and X₆ are each independently of the others oxygen or sulfur;

n₁, n₂, n₃ and n₄ are each independently of the others 0, 1, 2, 3 or 4; with the provisos that at least one of R₁, R₂ and A is different from hydrogen; and that when R₅₃ is hydrogen, R₅₄ is different from C₁ -C₄ alkyl; and the salts and stereoisomers thereof.

In the above definitions, halogen is to be understood as being fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine.

Suitable alkyl groups are straight-chained or branched, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and the various isomeric pentyl, hexyl, heptyl, octyl, nonyl and decyl radicals.

Suitable as haloallcyl are alkyl groups mono- or poly-substituted, especially mono- to tri-substituted, by halogen, wherein halogen is individually bromine or iodine, and especially fluorine or chlorine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl; preferably difluorochloromethyl, trifluoromethyl, dichlorofluoromethyl and trichloromethyl.

Alkoxy is, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy, ethoxy and isopropoxy.

Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, trifluoromethoxy and 2-chloroethoxy.

Alkylthio is, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio or isomeric pentylthio, preferably methylthio and ethylthio.

Alkenyl is to be understood as being straight-chained or branched alkenyl, such as vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pentenyl, 2-hexenyl or 3-heptenyl. Alkenyl radicals having a chain length of from 2 to 4 carbon atoms are preferred.

The alkynyl radicals appearing in the definitions of the substituents may be straight-chained or branched, such as ethynyl, propargyl, 3-butynyl, 1-methylpropargyl, 1-pentynyl or 2-hexynyl. Ethynyl and propargyl are preferred.

Cycloalkyl is, for example, cyclopropyl, dimethylcyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl or cycloheptyl, but preferably cyclopropyl, cyclopentyl or cyclohexyl.

Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl or n-butoxycarbonyl, preferably methoxycarbonyl or ethoxycarbonyl.

Alkoxyalkyl is, for example, methoxymethyl, ethoxymethyl, propoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, methoxypropyl, ethoxypropyl or propoxypropyl.

Alkylthioalkyl is, for example, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl or isopropylthioethyl.

Alkylaminoalkyl is, for example, methylaminoethyl, dimethylaminoethyl, ethylaminoethyl or diethylaminoethyl.

Cyanoalkyl is, for example, cyanomethyl, cyanoethyl or cyanopropyl.

Halocycloalkyl is, for example, 2,2-dichlorocyclopropyl or pentachlorocyclohexyl.

Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl or butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

Phenyl, also as part of a substituent such as phenoxy, phenylthio, phenoxycarbonyl, phenylaminocarbonyl, benzyl or benzoyl, can generally be unsubstituted or substituted. The substituents may be in the ortho-, meta- and/or para-position(s). Preferred substituent positions are the ortho- and para-positions to the ring-linkage point. Preferred substituents are halogen atoms.

In the further substituents that are composed of several basic elements, the elements are as defined above by way of example.

The salts of the compounds of formula I having acid protons, especially of the derivatives having carboxylic acid groups (A═--C(O)--X₄ R₅ wherein X₄ is oxygen and R₅ is hydrogen), are, for example, alkali metal salts, such as sodium and potassium salts; alkaline earth metal salts, such as calcium and magnesium salts; ammonium salts, i.e. unsubstituted ammonium salts and mono- or poly-substituted ammonium salts, for example triethylammonium and methylammonium salts; or salts with other organic bases.

Examples of amines suitable for salt formation are primary, secondary and tertiary aliphatic and aromatic amines, such as methylamine, ethylamine, n-propylamine, isopropylamine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methylhexylamine, methyl-nonylamine, methyl-pentadecylamine, methyl-octadecylamine, ethyl-butylamine, ethyl-heptylamine, ethyl-octylamine, hexyl-heptylamine, hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethylethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, diethanolamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine; heterocyclic amines, such as pyridine, quinoline, isoquinoline, morpholine, thiomorpholine, N-methylmorpholine, N-methyl-thiomorpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, such as anilines, methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines, benzidines, naphthylamines and o,m,p-chloroanilines.

Because at least one asymmetric carbon atom may be present in the compounds of formula I, for example in the ester and ether derivatives having substituted aliphatic and alicyclic groups, the compounds may occur both as optically active individual isomers and in the form of racemic mixtures. In the present invention, the compounds of formula I are to be understood as including both the pure optical antipodes and the racemates. Unless the individual optical antipodes are referred to specifically, there are to be understood by the formula given those racemic mixtures that are formed in the preparation process indicated. If an aliphatic C═C or C═N double bond is present, geometric isomerism may also occur.

Preference is given to compounds of formula I wherein Z is oxygen.

Preference is likewise given to compounds of formula Ia ##STR7## wherein Z, A, R₁, R₂, R₅₃ and R₅₄ are as defined for formula I.

Of those compounds, special preference is given to those wherein A is ##STR8## X₃ being especially sulfur and R₄ being C₁ -C₆ alkyl substituted by C₁ -C₆ alkoxycarbonyl.

In especially preferred compounds of formula Ia, R₁ and R₂ are halogen; R₁ is especially fluorine and R₂ is especially chlorine.

The preferred compounds likewise include those of formula Ib ##STR9## wherein Z, R₁₉, R₂₂, X₁, R₅₀, R₅₃, R₅₄ and n₁ are as defined for formula I.

Of those compounds, special preference is given to those wherein R₁₉ is C₁ -C₄ alkyl, C₃ -or C₄ -alkenyl, C₃ - or C₄ -haloalkenyl, C₃ -C₆ alkynyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, cyano-C₁ -C₄ alkyl, C₁ -C₆ alkoxycarbonyl-C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl, C₃ -C₆ cycloalkyl-C₁ -C₄ alkyl, benzyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, C₁ -C₄ alkylaminocarbonyl-C₁ -C₄ alkyl, di-C₁ -C₄ alkylaminocarbonyl-C₁ -C₄ alkyl, C₁ -C₄ alkoxycarbonyl or C₁ -C₄ alkylcarbonyl.

Of those compounds, preference is given especially to those wherein Z is oxygen; R₁₉ is C₁ -C₃ alkyl, C₁ -C₃ alkoxycarbonyl-C₁ - or-C₂ -alkyl or C₃ - or C₄ -alkynyl; R₂₂ is hydrogen or fluorine; R₅₀ is hydrogen; and n₁ is 0 or 1.

Compounds of formula I wherein R₅₃ and R₅₄ are C₁ -C₄ alkyl are especially important.

Of those compounds, those of formula I wherein R₅₃ and R₅₄ are each independently of the other methyl or ethyl are very especially important.

Compounds of formula I wherein R₅₃ and R₅₄, together with the carbon atom to which they are bonded, form an unsubstituted 3- or 5-membered ring are also very important.

Compounds of formula I wherein R₅₃ is hydrogen; and R₅₄ is C₁ -C₃ alkoxy, C₃ -C₅ alkenyl-oxy, C₃ -C₅ alkynyloxy or C₁ -C₃ haloalkoxy are likewise of great importance.

Of those compounds, preference is given especially to those wherein R₅₄ is C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy. In particular, of those compounds, those wherein R₅₄ is methoxy, isopropoxy or difluoromethoxy are of very great importance.

Individual compounds from the scope of formula I that may be mentioned are:

8-(4-chloro-2-fluoro-5-isopropoxy-phenylimino)-3,3-dimethyl-7-thia-1,5-diazabicyclo-[3.3.0]octan-6-one;

8-(4-chloro-2-fluoro-5-isopropoxy-phenylimino)-3-methoxy-7-thia-1,5-diazabicyclo[3.3.0]octan-6-one;

8-(4-chloro-2-fluoro-5-isopropoxy-phenylimino)-3-difluoromethoxy-7-thia-1,5-diazabicyclo[3.3.01octan-6-one; and

8-(4-chloro-2-fluoro-5-isopropoxy-phenylimino)-3,3-ethanediyl-7-thia-1,5-diazabicyclo[3.3.0]octan-6-one.

The process according to the invention for the preparation of a compound of formula I ##STR10## wherein Z, W, R₅₃ and R₅₄ are as defined for formula I, is carried out analogously to known processes and comprises converting an isothiocyanate of formula II

    S═C═N--W                                           (II),

wherein W is as defined for formula I, with a compound of formula III ##STR11## wherein R₅₃ and R₅₄ are as defined for formula I, into a compound of formula IV ##STR12## and then reacting the latter with a compound of formula V

    CZCl.sub.2                                                 (V),

wherein Z is oxygen or sulfur.

The reaction of the isothiocyanates of formula H with the compounds of formula III is advantageously carried out in an inert organic solvent at temperatures of from -5° C. to the boiling temperature of the solvent, especially from 0° to +50° C., preferably at room temperature. Examples of suitable solvents for this reaction are toluene, xylenes, ethyl acetate and acetonitrile.

The reaction of a compound of formula IV with a compound of formula V is advantageously carried out in an inert organic solvent at low temperatures, preferably from 0° to +50° C., especially from 0° to +15° C.

The starting compounds of formulae II and HI required for the preparation process according to the invention are either known or they can be prepared analogously to processes known from the literature. The preparation of such compounds from 1,3-dibromopropanes and hydrazine is described, for example, in J. Am. Chem. Soc. 88, 3959-3963 (1966).

Compounds of formula IIIa ##STR13## wherein R₅₃ is hydrogen or C₁ -C₆ alkyl; and R₅₄ ' is C₁ -C₆ alkyl; or R₅₃ and R₅₄ ', together with the carbon atom to which they are bonded, form an unsubstituted 3-, 4-, 5- or 6-membered saturated ring, can be prepared in accordance with Reaction Scheme 1. ##STR14## Compounds of formula IIIb ##STR15## wherein R is C₁ -C₆ alkyl, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl or C₁ -C₆ haloalkyl, can be prepared in accordance with Reaction Scheme 2. ##STR16##

The isothiocyanates of formula II are known or can be prepared analogously to known processes. Such compounds are described, for example, in EP-A-0 304 920, EP-A-0 238 711, EP-A-0 409 025, EP-A-0 373 461, EP-A-0 311 135 and DE-OS-3 724 098.

The compounds of formula I are generally used successfully at rates of application of from 0.001 to 2 kg/ha, especially from 0.005 to 1 kg/ha. The concentration required to achieve the desired effect can be determined by experiment. It is dependent upon the type of action, the stage of development of the crop plant and of the weed, and also upon the application (place, time, method) and, in dependence on those parameters, can vary within wide limits.

When used at relatively low rates of application, the compounds of formula I are distinguished by growth-inhibiting and herbicidal properties that make them outstandingly suitable for use in crops of useful plants, especially in cereals, maize, rape, soybeans, rice and cotton, the use thereof in soybean crops being very especially preferred.

The invention relates also to herbicidal compositions comprising a novel compound of formula I, and to methods of inhibiting plant growth.

Various methods and techniques are suitable for using a compound of formula I or a composition comprising such a compound as active ingredient for regulating plant growth. The following are examples thereof:

i) Seed dressing

a) Dressing the seeds with a wettable powder formulation of an active ingredient by shaking in a vessel until the formulation is evenly distributed over the surface of the seeds (dry dressing). Up to 4 g of a compound of formula I (in the case of a 50 % formulation: up to 8.0 g of wettable powder) are used per 1 kg of seed.

b) Dressing the seeds with an emulsifiable concentrate of the active ingredient or with an aqueous solution of a wettable powder formulation of a compound of formula I according to method a) (wet dressing).

c) Dressing by immersing the seeds in a mixture comprising up to 1000 ppm of a compound of formula I for 1 to 72 hours and, if desired, subsequently drying the seeds (seed soaking).

Dressing the seed or treating the germinated seedling are naturally the preferred methods of application since the active ingredient treatment is directed wholly at the target crop. Normally 0.001 g to 4.0 g of active ingredient are used per 1 kg of seed, although, depending on the method employed, which also allows the addition of other active ingredients or micronutrients, amounts that exceed or fall short of the specified concentration limits may be employed (repeat dressing).

ii) Controlled release of active ingredient

A solution of the active ingredient is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and allowed to dry. If desired, a coating may be applied (coated granules) that allows the active ingredient to be released in metered amounts over a specific period of time.

The compounds of formula I are used in unmodified form, as obtainable from synthesis, or preferably together with the adjuvants conventionally employed in formulation technology, and are therefore formulated in known manner, e.g. into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules and also encapsulations in, e.g. polymer substances. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The formulations, i.e. the compositions, preparations or mixtures comprising the compound (active ingredient) of formula I and, where appropriate, one or more solid or liquid adjuvants, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, such as mixtures of alkylbenzenes, e.g. xylene mixtures or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons, such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols, such as ethanol, propanol or butanol; glycols and their ethers and esters, such as propylene glycol or dipropylene glycol ether; ketones, such as cyclohexanone, isophorone or diacetone alcohol; strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water; vegetable oils and esters thereof, such as rape oil, castor oil or soybean oil; and, where appropriate, also silicone oils. The solid carriers used e.g. for dusts and dispersible powders are normally natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonitc; and suitable nonsorbent carriers are, for example, calcite or sand. In addition, a great number of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues.

Depending on the nature of the compound of formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term "surfactants" will also be understood as comprising mixtures of surfactants.

Both so-called water-soluble soaps and water-soluble synthetic surface-active compounds are suitable anionic surfactants.

Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C₁₀ -C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil. Fatty acid methyltaurin salts may also be mentioned.

More frequently, however, so-called synthetic surfactants are used, especially fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty alcohol sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain a C₈ -C₂₂ alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts. The sulfonated benzLmidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates arc the sodium, calcium or triethanolaminc salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a condensate of naphthalenesulfonic acid and formaldehyde.

Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids.

Non-ionic surfactants arc preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphafic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxy-polyethoxyethanol, polyethylene glycol and octylphenoxy-polyethoxyethanol.

Fatty acid esters of polyoxyethylene sorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable.

Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one C₈ -C₂₂ alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, e.g. stearyltrimethyl-ammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in formulation technology are described inter alia in the following publications:

"Mc Cutcheon's Detergents and Emulsifiers Annual", Mc Publishing Corp., Glen Rock, N.J., 1988.

M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-1981.

Dr. ttelmut Stache "Tensid-Taschenbuch" (Surfactant Flandbook), Carl Hanser Verlag, Munich/Vienna 1981.

The herbicidal compositions usually comprise 0.1 to 99 %, preferably 0.1 to 95 %, of a compound of formula I, 1 to 99 % of a solid or liquid adjuvant, and 0 to 25 %, preferably 0.1 to 25 %, of a surfactant.

Whereas commercial products are preferably formulated as concentrates, the end user will normally employ dilute formulations.

The compositions may also comprise further ingredients such as stabilisers, e.g. vegetable oils and epoxidised vegetable oils (epoxidised coconut oil, rape oil or soybean oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients for obtaining special effects.

Preferred formulations have especially the following composition (throughout, percentages are by weight)

    ______________________________________                                         Emulsifiable concentrates:                                                     active ingredient:                                                                            1 to 90%,  preferably 5 to 50%                                  surface-active agent:                                                                         5 to 30%,  preferably 10 to 20%                                 liquid carrier:                                                                               15 to 94%, preferably 70 to 85%                                 Dusts:                                                                         active ingredient:                                                                            0.1 to 10%,                                                                               preferably 0.1 to 1%                                 solid carrier: 99.9 to 90%,                                                                              preferably 99.9 to 99%                               Suspension concentrates:                                                       active ingredient:                                                                            5 to 75%,  preferably 10 to 50%                                 water          94 to 24%, preferably 88 to 30%                                 surface-active agent:                                                                         1 to 40%,  preferably 2 to 30%                                  Wettable powders:                                                              active ingredient:                                                                            0.5 to 90%,                                                                               preferably 1 to 80%                                  surface-active agent:                                                                         0.5 to 20%,                                                                               preferably 1 to 15%                                  solid carrier: 5 to 95%,  preferably 15 to 90%                                 Granules:                                                                      active ingredient                                                                             0.5 to 30%,                                                                               preferably 3 to 15%                                  solid carrier  99.5 to 70%,                                                                              preferably 97 to 85%                                 ______________________________________                                    

A. Preparation Examples Example P1 Preparation of 2,3-diazaspim[4.2]cycloheptane-2,3-dicarboxylic acid tert-butyl ester ##STR17##

At a maximum of 30° C., 9.1 g of hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester in 20 ml of N,N-dimethylformamide are added dropwise to a suspension of 3.1 g of a 60 % sodium hydride dispersion in 40 ml of N,N-dimethylformamide. After stirring for 1 hour at 22° C., 10.0 g of 1,1-cyclopropane dimethanol dimethanesulfonate in 20 ml of N,N-dimethylformamide are added dropwise in the form of a suspension to the reaction mixture, which is then stirred for 18 hours at 22° C. The resulting yellow suspension is poured onto 700 ml of ice water and the product that has precipitated is suction-filtered and dried in a desiccator to yield 6.8 g of the desired product, 2,3-diazaspiro[4.2]cyclo-heptane-2,3-dicarboxylic acid tert-butyl ester in the form of wax-like crystals; m.p. 60°-70° C.

Example P2 Preparation of 2,3-diazaspiro[4.2]cycloheptane dihydrobromide ##STR18##

At 0-5° C., 50 ml of a solution of hydrogen bromide in acetic acid (33 %) are added dropwise to a solution of 29.8 g of 2,3-diazaspiro[4.2]cycloheptane-2,3-dicarboxylic acid tertbutyl ester in 500 ml of diethyl ether. After stirring for 3 hours at 0°-5° C., the precipitate that has formed is suction-filtered, washed with diethyl ether and dried in vacuo to yield 23.3 g of the desired 2,3-diazaspiro[4.2]cycloheptane dihydrobromide in the form of white, hygroscopic crystals.

Example P3 Preparation of 4-hydroxypyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester ##STR19##

46.4 g of hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester, 69.0 g of potassium carbonate, 3.3 g of potassium iodide, 20 ml of tetrabutylammonium fluoride (1 molar solution in tetrahydrofuran) and 21 ml of epibromohydrin are boiled under reflux for 48 hours in 400 ml of ethyl methyl ketone. The resulting suspension is concentrated, and 500 ml of diethyl ether are added thereto; the reaction mixture is then filtered and the tiltrate is concentrated. Purification of the crude product by means of column chromatography yields 27.1 g of the desired 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in the form of white crystals; m.p. 100°-102° C.

Example P4 Preparation of 4-hydroxy-pyrazolidine dihydrobromide ##STR20##

At 22° C., 24 ml of a solution of hydrogen bromide in acetic acid (33 %) are added dropwise to a solution of 11.5 g of 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in 160 ml of diethyl ether. After stirring for 3 hours at 22° C., 200 ml of diethyl ether are added and the product that has precipitated is filtered off and dried under a high vacuum at 50° C. to yield 9.4 g of 4-hydroxy-pyrazolidine dihydrobromide in the form of light brown hygroscopic crystals.

Example P5 Preparation of 4-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester ##STR21##

At 0°-5° C., 1.2 g of a sodium hydride dispersion (80 %) are added in portions to a solution of 8.6 g of 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in 90 ml of N,N-dimethylformamide. After stiffing for 30 minutes at 0°-5° C., a solution of 2.5 ml of methyl iodide in 10 ml of N,N-dimethylformamide is added dropwise thereto. Stirring is then continued for 3 hours at 0°-5° C. and then 500 ml of diethyl ether are added thereto. The organic phase is washed with water, dried over sodium sulfate and concentrated to yield 8.0 g of the desired product, 4-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tertbutyl ester, in the form of a yellow oil.

Example P6

4-Methoxy-pyrazolidine dihydrobromide is obtained analogously to Example P5 using 4-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester. ##STR22##

Example P7 Preparation of 4-difluoromethoxy-pyrazolidine- N,N'-dicarboxylic acid di-tert-butyl ester ##STR23##

0.2 g of tetrabutylammonium fluoride and 5.6 g of potassium hydroxide powder are added to a solution of 6.9 g of 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in 60 ml of tetrahydrofuran. At a maximum of 45° C., 8.0 g of chlorodifluoromethane are introduced. The reaction solution is then filtered, concentrated and purified by means of column chromatography to yield 2.7 g of the desired product, 4-difluoromethoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester, in the form of a yellow oil.

Example P8

4-Difluoromethoxy-pyrazolidine dihydrobromide is obtained analogously to Example P5 using 4-difluoromethoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester. ##STR24##

Example P9 Preparation of 4,4-dimethyl-pyrazolidine N,N'-dicarboxylic acid di-tert-buty1 ester ##STR25##

41.8 g of hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester, 74.5 g of potassium carbonate, 52.0 g of 2,2-dimethyl-1,3-propanediol dimethanesulfonate and 2.0 g of potassium iodide are stirred for 48 hours at 120°-130° C. in 360 ml of N,N-dimethylformamide. The reaction mixture is then concentrated; diethyl ether is added and the organic phase is washed with water. Mter drying over sodium sulfate, the reaction mixture is concentrated and purified by means of column chromatography to yield 1.1 g of the desired product, 4,4-dimethyl-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester, in the form of white crystals.

Example P 10

4,4-Dimethylpyrazolidine dihydrobromide is obtained analogously to Example P5 using 4,4-dimethyl-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester. ##STR26##

Example P 11 Preparation of α-[2-chloro-4-fiuoro-5-(4-methoxypyrazolidinylthio-carbonylamino)-phenylthio]-acetic acid methyl ester ##STR27##

4.2 ml of triethylamine are added to a suspension of 2.65 g of 4-methoxypyrazolidine dihydrobromide in 50 ml of ethyl acetate and the reaction mixture is stirred for 10 minutes at 22° C. 2.35 g of 4-chloro-2-fiuoro-5-methoxycarbonylmethyl-thiophenyl isothiocyanate are then added thereto and the reaction mixture is stirred overnight at 22° C. The organic phase is washed with water, dried and concentrated. The crystalline product, α-[2-choro-4-fluoro-5-(4-methoxypyrazolidinyl-thiocarbonylamino)-phenylthio]-acetic acid methyl ester, is obtained in a yield of 3.0 g; m.p. >90° C. (decomposition).

Example P12 Preparation of 8-(4-chloro-2-fluoro-5-methoxycarbonylmethylthio-phenyl-imino)-3-methoxy-7-thia-1,5-diazabicyclo[3.3.0]octan-6-one ##STR28##

At 0°-5° C., 4.2 ml of phosgene solution in toluene (20%) are added to a solution of 2.8 g of α-[2-chloro-4-fluoro-5-(4-methoxypyrazolidinyl-thiocarbonylamino)-phenylthio]-acetic acid methyl ester in 20 ml of toluene. After stirring for 2 hours at 22° C., the organic phase is washed with water, dried and concentrated. The product is purified by means of column chromatography to yield 2.21 g of the desired product, 8-(4-chloro-2-fluoro-5-methoxy-carbonylmethylthio-phenylimino)-3-methoxy-7-thia-1,5-diazabicyclo[3.3.0]octan-6-one, in the form of a yellow oil.

Example P 13 Preparation of 4-hydroxy-N-[(2-fluoro-4-chloro-5-isopropoxy)-phenyl]pyrazolidine-2-thioamide ##STR29##

At 0°-5° C., 2.8 ml of triethylamine are added dropwise to a suspension of 2.0 g of 4-hydroxy-pyrazolidine dihydrobromide in 25 ml of tetrahydrofuran. After stirring for 10 minutes at 22° C., 2.0 g of 4-chloro-2-fluoro-5-isopropoxy-phenyl isothiocyanate in 5 ml of tetrahydrofuran are added dropwise thereto and the reaction mixture is stiffed for 3 hours. The reaction mixture is concentrated; ethyl acetate is added and the organic phase is washed with water, dried and concentrated. The product is purified by crystallisation from petroleum ether. The desired product, 4-hydroxy-N-[(2-fluoro-4-chloro-5-isopropoxy)phenyl]-pyrazolidine-2-thioamide, is obtained in the form of white crystals in a yield of 2.2 g; m.p. 151°-153° C. (decomposition).

Example P 14 Preparation of 8-(4-chloro-2-fluoro-5-isopropoxyphenylimino)-3-hydroxy-7-thia-1,5-diazabicyclo3.3.0]octan-6-one ##STR30##

At 0°-5° C., 3.4 ml of phosgene dissolved in toluene (20 %) are added dropwise to a solution of 2.1 g of 4-chloro-2-fluoro-5-isopropoxy-N-(4-hydroxypyrazolidinyl-thiocarbonyl)-aniline in 50 ml of dichloromethane. After stirring for 1 hour at 22° C, the reaction mixture is concentrated and then ethyl acetate is added thereto. The organic phase is washed with water, dried and concentrated and the resulting residue is purified by means of column chromatography to yield 1.95 g of the desired product, 8-(4-chloro-2-fluoro-5-isopropoxyphenylimino)-3-hydroxy-7-thia- 1,5-diazabicyclo[3.3.0]octan-6-one, in the form of a resin.

The compounds of formula I listed in the following Tables 1 to 15 are prepared in analogous manner.

                                      TABLE 1                                      __________________________________________________________________________     Compounds of formula Ic:                                                        ##STR31##                                     (Ic)                            Comp. No.                                                                             R.sub.1                                                                           R.sub.2                                                                            A                     phys. data                                 __________________________________________________________________________     1.001  F  Cl  H                                                                1.002  F  Cl  CN                                                               1.003  F  Cl  NO.sub.2                                                         1.004  F  Cl  COOH                                                             1.005  F  Cl  COOCH.sub.3                                                      1.006  F  Cl  COOC.sub.2 H.sub.5                                               1.007  F  Cl  COOC.sub.3 H.sub.7                                               1.008  F  Cl  COOCH(CH.sub.3).sub.2                                            1.009  F  Cl  COOC.sub.4 H.sub.9                                               1.010  F  Cl                                                                                  ##STR32##                                                       1.011  F  Cl                                                                                  ##STR33##                                                       1.012  F  Cl  COOC.sub.5 H.sub.11                                              1.013  F  Cl  COOCH.sub.2CH.sub.2OCH.sub.3                                     1.014  F  Cl  COOCH.sub.2CH.sub.2OC.sub.2 H.sub.5                              1.015  F  Cl  COOCH(CH.sub.3)CH.sub.2OCH.sub.3                                 1.016  F  Cl  COOCH.sub.2CH.sub.2SCH.sub.3                                     1.017  F  Cl  COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                 1.018  F  Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.2 H.sub.5                          1.019  F  Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.3 H.sub.7                          1.020  F  Cl                                                                                  ##STR34##                                                       1.021  F  Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.4 H.sub.9                          1.022  F  Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.5 H.sub.11                         1.023  F  Cl                                                                                  ##STR35##                                                       1.024  F  Cl                                                                                  ##STR36##                                                       1.025  F  Cl  CONH.sub.2                                                       1.026  F  Cl  CONHCH.sub.3                                                     1.027  F  Cl                                                                                  ##STR37##                                                       1.028  F  Cl                                                                                  ##STR38##                                                       1.029  F  Cl                                                                                  ##STR39##                                                       1.030  F  Cl  CONHCH.sub.2CHCH.sub.2                                           1.031  F  Cl  CON(CH.sub.2CHCH.sub.2).sub.2                                    1.032  F  Cl                                                                                  ##STR40##                                                       1.033  F  Cl                                                                                  ##STR41##                                                       1.034  F  Cl                                                                                  ##STR42##                                                       1.035  F  Cl                                                                                  ##STR43##                                                       1.036  F  Cl                                                                                  ##STR44##                                                       1.037  F  Cl                                                                                  ##STR45##                                                       1.038  F  Cl  COOCH.sub.2CH.sub.2Cl                                            1.039  F  Cl  COOCH.sub.2CN                                                    1.040  F  Cl                                                                                  ##STR46##                                                       1.041  F  Cl  COOCH.sub.2CHCH.sub.2                                            1.042  F  Cl  COOCH.sub.2CHCHCl                                                1.043  F  Cl                                                                                  ##STR47##                                                       1.044  F  Cl  COOCH.sub.2CCH                                                   1.045  F  Cl                                                                                  ##STR48##                                                       1.046  F  Cl                                                                                  ##STR49##                                                       1.047  F  Cl                                                                                  ##STR50##                                                       1.048  F  Cl                                                                                  ##STR51##                                                       1.049  F  Cl                                                                                  ##STR52##                                                       1.050  F  Cl                                                                                  ##STR53##                                                       1.051  F  Cl                                                                                  ##STR54##                                                       1.052  F  Cl                                                                                  ##STR55##                                                       1.053  F  Cl  COSCH.sub.3                                                      1.054  F  Cl  COSC.sub.2 H.sub.5                                               1.055  F  Cl  COSC.sub.3 H.sub.7                                               1.056  F  Cl  COSCH.sub.2CHCH.sub.2                                            1.057  F  Cl  COSCH.sub.2COOCH.sub.3                                           1.058  F  Cl  COSCH.sub.2COOC.sub.2 H.sub.5                                    1.059  F  Cl  COSCH.sub.2COOC.sub.5 H.sub.11                                   1.060  F  Cl                                                                                  ##STR56##                                                       1.061  F  Cl                                                                                  ##STR57##                                                       1.062  F  Cl                                                                                  ##STR58##                                                       1.063  F  Cl  COSCH.sub.2CH.sub.2COOCH.sub.3                                   1.064  F  Cl  COSCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                          1.065  F  Cl  COOCH.sub.2COOCH.sub.3                                           1.066  F  Cl                                                                                  ##STR59##                                                       1.067  F  Cl  COOCH.sub.2COOC.sub.5 H.sub.11                                   1.068  F  Cl  COOCH.sub.2CH.sub.2Si(CH.sub.3).sub.3                            1.069  F  Cl  COONa                                                            1.070  F  Cl                                                                                  ##STR60##                                                       1.071  F  Cl  OH                                                               1.072  F  Cl  OCH.sub.3                                                        1.073  F  Cl  OC.sub.2 H.sub.5                                                 1.074  F  Cl  OC.sub.3 H.sub.7                                                 1.075  F  Cl                                                                                  ##STR61##            m.p. 76-77° C.                      1.076  F  Cl  OC.sub.4 H.sub.9                                                 1.077  F  Cl                                                                                  ##STR62##                                                       1.078  F  Cl                                                                                  ##STR63##                                                       1.079  F  Cl  OCH.sub.2 CHCH.sub.2                                             1.080  F  Cl                                                                                  ##STR64##                                                       1.081  F  Cl  OCH.sub.2 CHCHCl                                                 1.082  F  Cl  OCH.sub.2 CCH                                                    1.083  F  Cl                                                                                  ##STR65##                                                       1.084  F  Cl  OCH.sub.2COOCH.sub.3                                             1.085  F  Cl  OCH.sub.2COOC.sub.5 H.sub.11                                     1.086  F  Cl                                                                                  ##STR66##                                                       1.087  F  Cl  OCH.sub.2COOC.sub.2 H.sub.5                                      1.088  F  Cl                                                                                  ##STR67##                                                       1.089  F  Cl  O CH.sub.2CH.sub.2OCH.sub.3                                      1.090  F  Cl                                                                                  ##STR68##                                                       1.091  F  Cl                                                                                  ##STR69##                                                       1.092  F  Cl                                                                                  ##STR70##                                                       1.093  F  Cl  OCH.sub.2CH.sub.2Cl                                              1.094  F  Cl  OCH.sub.2CN                                                      1.095  F  Cl                                                                                  ##STR71##                                                       1.096  F  Cl  SCH.sub.3                                                        1.097  F  Cl  SC.sub.2 H.sub.5                                                 1.098  F  Cl  SC.sub.3 H.sub.7                                                 1.099  F  Cl                                                                                  ##STR72##                                                       1.100  F  Cl  SCH.sub.2CHCH.sub.2                                              1.101  F  Cl                                                                                  ##STR73##                                                       1.102  F  Cl  SCH.sub.2CHCHCl                                                  1.103  F  Cl  SCH.sub.2CCH                                                     1.104  F  Cl                                                                                  ##STR74##                                                       1.105  F  Cl  SCH.sub.2COOCH.sub.3                                             1.106  F  Cl  SCH.sub.2COOC.sub.2 H.sub.5                                      1.107  F  Cl  SCH.sub.2COOC.sub.5 H.sub.11                                     1.108  F  Cl                                                                                  ##STR75##                                                       1.109  F  Cl                                                                                  ##STR76##                                                       1.110  F  Cl  SCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                            1.111  F  Cl                                                                                  ##STR77##                                                       1.112  F  Cl                                                                                  ##STR78##                                                       1.113  F  Cl                                                                                  ##STR79##                                                       1.114  F  Cl                                                                                  ##STR80##                                                       1.115  F  Cl                                                                                  ##STR81##                                                       -1.116 F  Cl                                                                                  ##STR82##                                                       1.117  F  Cl                                                                                  ##STR83##                                                       1.118  F  Cl                                                                                  ##STR84##                                                       1.119  F  Cl                                                                                  ##STR85##                                                       1.120  F  Cl                                                                                  ##STR86##                                                       1.121  F  Cl                                                                                  ##STR87##                                                       1.122  F  Cl                                                                                  ##STR88##                                                       1.123  F  Cl                                                                                  ##STR89##                                                       1.124  F  Cl                                                                                  ##STR90##                                                       1.125  F  Cl                                                                                  ##STR91##                                                       1.126  F  Cl                                                                                  ##STR92##                                                       1.127  F  Cl                                                                                  ##STR93##                                                       1.128  F  Cl                                                                                  ##STR94##                                                       1.129  F  Cl                                                                                  ##STR95##                                                       1.130  F  Cl                                                                                  ##STR96##                                                       1.131  F  Cl                                                                                  ##STR97##                                                       1.132  F  Cl                                                                                  ##STR98##                                                       1.133  F  Cl                                                                                  ##STR99##                                                       1.134  F  Cl                                                                                  ##STR100##                                                      1.135  F  Cl                                                                                  ##STR101##                                                      1.136  F  Cl                                                                                  ##STR102##                                                      1.137  F  Cl                                                                                  ##STR103##                                                      1.138  F  Cl                                                                                  ##STR104##                                                      1.139  F  Cl                                                                                  ##STR105##                                                      1.140  F  Cl                                                                                  ##STR106##                                                      1.141  F  Cl                                                                                  ##STR107##                                                      1.142  F  Cl                                                                                  ##STR108##                                                      1.143  F  Cl                                                                                  ##STR109##                                                      1.144  F  Cl                                                                                  ##STR110##                                                      1.145  F  Cl                                                                                  ##STR111##                                                      1.146  F  Cl  NHSO.sub.2CH.sub.3                                               1.147  F  Cl  NHSO.sub.2C.sub.2 H.sub.5                                        1.148  F  Cl  NHSO.sub.2Cl                                                     1.149  F  Cl                                                                                  ##STR112##                                                      1.150  F  Cl                                                                                  ##STR113##                                                      1.151  H  Cl  COOH                  m.p. >230° C. (decomp.)             1.152  H  Cl  COOCH.sub.3           m.p. 104-106° C.                    1.153  H  Cl                                                                                  ##STR114##           m.p. 90-91° C.                      1.154  H  Cl  COOC.sub.5 H.sub.11                                              1.155  H  Cl  COOCH.sub.2CH.sub.2OCH.sub.3                                     1.156  H  Cl  COOCH.sub.2SCH.sub.3                                             1.157  H  Cl  COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                 1.158  H  Cl                                                                                  ##STR115##                                                      1.159  H  Cl                                                                                  ##STR116##                                                      1.160  H  Cl                                                                                  ##STR117##                                                      1.161  H  Cl                                                                                  ##STR118##                                                      1.162  H  Cl                                                                                  ##STR119##                                                      1.163  H  Cl                                                                                  ##STR120##                                                      1.164  H  Cl                                                                                  ##STR121##                                                      1.165  H  Cl  SC.sub.3 H.sub.7                                                 1.166  H  Cl  COOCH.sub.2COOCH.sub.3                                           1.167  H  Cl  COOCH(CH.sub.3)COOCH.sub.3                                       1.168  H  Cl  COSCH.sub.2COOCH.sub.3                                           1.169  H  Cl  COSCH(CH.sub.3)COOCH.sub.3                                       1.170  H  Cl  OH                                                               1.171  H  Cl  OCH.sub.3                                                        1.172  H  Cl  OC.sub.2 H.sub.5                                                 1.173  H  Cl                                                                                  ##STR122##                                                      1.174  H  Cl  OCH.sub.2CCH                                                     1.175  H  Cl  OCH.sub.2CHCHCl                                                  1.176  H  Cl                                                                                  ##STR123##                                                      1.177  H  Cl                                                                                  ##STR124##                                                      1.178  H  Cl  OCH.sub.2COOCH.sub.3                                             1.179  H  Cl  OCH.sub.2COOC.sub.2 H.sub.5                                      1.180  H  Cl  OCH(CH.sub.3)COOCH.sub.3                                         1.181  H  Cl  SH                                                               1.182  H  Cl  SCH.sub.3                                                        1.183  H  Cl  SC.sub.2 H.sub.5                                                 1.184  H  Cl                                                                                  ##STR125##                                                      1.185  H  Cl  SCH.sub.2COOCH.sub.3                                             1.186  H  Cl  SCH(CH.sub.3)COOCH.sub.3                                         1.187  H  Cl  SCH.sub.2COOC.sub.2 H.sub.5                                      1.188  H  Cl                                                                                  ##STR126##                                                      1.189  H  Cl                                                                                  ##STR127##                                                      1.190  H  Cl                                                                                  ##STR128##                                                      1.191  H  Cl                                                                                  ##STR129##                                                      1.192  H  Cl                                                                                  ##STR130##                                                      1.193  H  Cl                                                                                  ##STR131##                                                      1.194  H  Cl                                                                                  ##STR132##                                                      1.195  H  Cl                                                                                  ##STR133##                                                      1.196  H  Cl                                                                                  ##STR134##                                                      1.197  H  Cl                                                                                  ##STR135##                                                      1.198  H  Cl                                                                                  ##STR136##                                                      1.199  H  Cl                                                                                  ##STR137##                                                      1.200  H  Cl                                                                                  ##STR138##                                                      1.201  H  Cl                                                                                  ##STR139##                                                      1.202  H  Cl  NHSO.sub.2C.sub.2 H.sub.5                                        1.203  H  Cl  NHSO.sub.2CH.sub.2Cl                                             1.204  F  CN  COOH                                                             1.205  F  CN                                                                                  ##STR140##                                                      1.206  F  CN                                                                                  ##STR141##                                                      1.207  F  CN  OCH.sub.2CCH                                                     1.208  F  CN  OCH(CH.sub.3)CCH                                                 1.209  F  CN  SCH.sub.2COOCH.sub.3                                             1.210  F  CN  SCH(CH.sub.3)COOCH.sub.3                                         1.211  F  CN  OCH.sub.2COOCH.sub.3                                             1.212  F  CN  OCH.sub.2COOC.sub.5 H.sub.11                                     1.213  F  CN  OCH(CH.sub.3)COOC.sub.2 H.sub.5                                  1.214  F  CN                                                                                  ##STR142##                                                      1.215  F  CN                                                                                  ##STR143##                                                      1.216  F  CN                                                                                  ##STR144##                                                      1.217  F  CN                                                                                  ##STR145##                                                      1.218  F  CN                                                                                  ##STR146##                                                      1.219  F  CN                                                                                  ##STR147##                                                      1.220  F  CN                                                                                  ##STR148##                                                      1.221  F  Br  COOH                                                             1.222  F  Br                                                                                  ##STR149##                                                      1.223  F  Br  OH                                                               1.224  F  Br                                                                                  ##STR150##                                                      1.225  F  Br  OCH.sub.2CCH                                                     1.226  F  Br  OCH(CH.sub.3)CCH                                                 1.227  F  Br  OCH.sub.2 COOCH.sub.3                                            1.228  F  Br  OCH.sub.2COOC.sub.5 H.sub.11                                     1.229  F  Br  SCH.sub.2COOCH.sub.3                                             1.230  F  Br                                                                                  ##STR151##                                                      1.231  F  Br                                                                                  ##STR152##                                                      1.232  F  Br                                                                                  ##STR153##                                                      1.233  F  Cl  SCH.sub.2 COOH        m.p. >120° C.                       __________________________________________________________________________                                         (decomp.)                             

                                      TABLE 2                                      __________________________________________________________________________     Compounds of formula Id:                                                        ##STR154##                         (Id)                                       Comp.                                                                          No. R.sub.1                                                                          R.sub.2                                                                            A                      phys. data                                    __________________________________________________________________________     2.001                                                                              F Cl  H                                                                    2.002                                                                              F Cl  CN                                                                   2.003                                                                              F Cl  NO.sub.2                                                             2.004                                                                              F Cl  COOH                                                                 2.005                                                                              F Cl  COOCH.sub.3                                                          2.006                                                                              F Cl  COOC.sub.2 H.sub.5                                                   2.007                                                                              F Cl  COOC.sub.3 H.sub.7                                                   2.008                                                                              F Cl  COOCH(CH.sub.3).sub.2                                                2.009                                                                              F Cl  COOC.sub.4 H.sub.9                                                   2.010                                                                              F Cl                                                                                  ##STR155##                                                          2.011                                                                              F Cl                                                                                  ##STR156##                                                          2.012                                                                              F Cl  COOC.sub.5 H.sub.11                                                  2.013                                                                              F Cl  COOCH.sub.2CH.sub.2OCH.sub.3                                         2.014                                                                              F Cl  COOCH.sub.2CH.sub.2OC.sub.2 H.sub.5                                  2.015                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2OCH.sub.3                                     2.016                                                                              F Cl  COOCH.sub.2CH.sub.2SCH.sub.3                                         2.017                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                     2.018                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.2 H.sub.5                              2.019                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.3 H.sub.7                              2.020                                                                              F Cl                                                                                  ##STR157##                                                          2.021                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.4 H.sub.9                              2.022                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.5 H.sub.11                             2.023                                                                              F Cl                                                                                  ##STR158##                                                          2.024                                                                              F Cl                                                                                  ##STR159##                                                          2.025                                                                              F Cl  CONH.sub.2                                                           2.026                                                                              F Cl  CONHCH.sub. 3                                                        2.027                                                                              F Cl                                                                                  ##STR160##                                                          2.028                                                                              F Cl                                                                                  ##STR161##                                                          2.029                                                                              F Cl                                                                                  ##STR162##                                                          2.030                                                                              F Cl  CONHCH.sub.2CHCH.sub.2                                               2.031                                                                              F Cl  CON(CH.sub.2CHCH.sub.2).sub.2                                        2.032                                                                              F Cl                                                                                  ##STR163##                                                          2.033                                                                              F Cl                                                                                  ##STR164##                                                          2.034                                                                              F Cl                                                                                  ##STR165##                                                          2.035                                                                              F Cl                                                                                  ##STR166##                                                          2.036                                                                              F Cl                                                                                  ##STR167##                                                          2.037                                                                              F Cl                                                                                  ##STR168##                                                          2.038                                                                              F Cl  COOCH.sub.2CH.sub.2Cl                                                2.039                                                                              F Cl  COOCH.sub.2CN                                                        2.040                                                                              F Cl                                                                                  ##STR169##                                                          2.041                                                                              F Cl  COOCH.sub.2CHCH.sub.2                                                2.042                                                                              F Cl  COOCH.sub.2CHCHCl                                                    2.043                                                                              F Cl                                                                                  ##STR170##                                                          2.044                                                                              F Cl  COOCH.sub.2CCH                                                       2.045                                                                              F Cl                                                                                  ##STR171##                                                          2.046                                                                              F Cl                                                                                  ##STR172##                                                          2.047                                                                              F Cl                                                                                  ##STR173##                                                          2.048                                                                              F Cl                                                                                  ##STR174##                                                          2.049                                                                              F Cl                                                                                  ##STR175##                                                          2.050                                                                              F Cl                                                                                  ##STR176##                                                          2.051                                                                              F Cl                                                                                  ##STR177##                                                          2.052                                                                              F Cl                                                                                  ##STR178##                                                          2.053                                                                              F Cl  COSCH.sub.3                                                          2.054                                                                              F Cl  COSC.sub.2 H.sub.5                                                   2.055                                                                              F Cl  COSC.sub.3 H.sub.7                                                   2.056                                                                              F Cl  COSCH.sub.2CHCH.sub.2                                                2.057                                                                              F Cl  COSCH.sub.2COOCH.sub.3                                               2.058                                                                              F Cl  COSCH.sub.2COOC.sub.2 H.sub.5                                        2.059                                                                              F Cl  COSCH.sub.2COOC.sub.5 H.sub.11                                       2.060                                                                              F Cl                                                                                  ##STR179##                                                          2.061                                                                              F Cl                                                                                  ##STR180##                                                          2.062                                                                              F Cl                                                                                  ##STR181##                                                          2.063                                                                              F Cl  COSCH.sub.2CH.sub.2COOCH.sub.3                                       2.064                                                                              F Cl  COSCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                              2.065                                                                              F Cl  COOCH.sub.2COOCH.sub.3                                               2.066                                                                              F Cl                                                                                  ##STR182##                                                          2.067                                                                              F Cl  COOCH.sub.2COOC.sub.5 H.sub.11                                       2.068                                                                              F Cl  COOCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                              2.069                                                                              F Cl  COONa                                                                2.070                                                                              F Cl                                                                                  ##STR183##                                                          2.071                                                                              F Cl  OH                                                                   2.072                                                                              F Cl  OCH.sub.3                                                            2.073                                                                              F Cl  OC.sub.2 H.sub.5                                                     2.074                                                                              F Cl  OC.sub.3 H.sub.7                                                     2.075                                                                              F Cl                                                                                  ##STR184##                                                          2.076                                                                              F Cl  OC.sub.4 H.sub.9                                                     2.077                                                                              F Cl                                                                                  ##STR185##                                                          2.078                                                                              F Cl                                                                                  ##STR186##                                                          2.079                                                                              F Cl  OCH.sub.2 CHCH.sub.2                                                 2.080                                                                              F Cl                                                                                  ##STR187##                                                          2.081                                                                              F Cl  OCH.sub.2 CHCHCl                                                     2.082                                                                              F Cl  OCH.sub.2 CCH                                                        2.083                                                                              F Cl                                                                                  ##STR188##                                                          2.084                                                                              F Cl  OCH.sub.2COOCH.sub.3                                                 2.085                                                                              F Cl  OCH.sub.2COOC.sub.5 H.sub.11                                         2.086                                                                              F Cl                                                                                  ##STR189##                                                          2.087                                                                              F Cl  OCH.sub.2COOC.sub.2 H.sub.5                                          2.088                                                                              F Cl                                                                                  ##STR190##                                                          2.089                                                                              F Cl  OCH.sub.2CH.sub.2OCH.sub.3                                           2.090                                                                              F Cl                                                                                  ##STR191##                                                          2.091                                                                              F Cl                                                                                  ##STR192##                                                          2.092                                                                              F Cl                                                                                  ##STR193##                                                          2.093                                                                              F Cl  OCH.sub.2CH.sub.2Cl                                                  2.094                                                                              F Cl  OCH.sub.2CN                                                          2.095                                                                              F Cl                                                                                  ##STR194##                                                          2.096                                                                              F Cl  SCH.sub.3                                                            2.097                                                                              F Cl  SC.sub.2 H.sub.5                                                     2.098                                                                              F Cl  SC.sub.3 H.sub.7                                                     2.099                                                                              F Cl                                                                                  ##STR195##                                                          2.100                                                                              F Cl  SCH.sub.2CHCH.sub.2                                                  2.101                                                                              F Cl                                                                                  ##STR196##                                                          2.102                                                                              F Cl  SCH.sub.2CHCHCl                                                      2.103                                                                              F Cl  SCH.sub.2CCH                                                         2.104                                                                              F Cl                                                                                  ##STR197##                                                          2.105                                                                              F Cl  SCH.sub.2COOCH.sub.3                                                 2.106                                                                              F Cl  SCH.sub.2COOC.sub.2 H.sub.5                                          2.107                                                                              F Cl  SCH.sub.2COOC.sub.5 H.sub.11                                         2.108                                                                              F Cl                                                                                  ##STR198##                                                          2.109                                                                              F Cl                                                                                  ##STR199##                                                          2.110                                                                              F Cl  SCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                                2.111                                                                              F Cl                                                                                  ##STR200##                                                          2.112                                                                              F Cl                                                                                  ##STR201##                                                          2.113                                                                              F Cl                                                                                  ##STR202##                                                          2.114                                                                              F Cl                                                                                  ##STR203##                                                          2.115                                                                              F Cl                                                                                  ##STR204##                                                          2.116                                                                              F Cl                                                                                  ##STR205##                                                          2.117                                                                              F Cl                                                                                  ##STR206##                                                          2.118                                                                              F Cl                                                                                  ##STR207##                                                          2.119                                                                              F Cl                                                                                  ##STR208##                                                          2.120                                                                              F Cl                                                                                  ##STR209##                                                          2.121                                                                              F Cl                                                                                  ##STR210##                                                          2.122                                                                              F Cl                                                                                  ##STR211##                                                          2.123                                                                              F Cl                                                                                  ##STR212##                                                          2.124                                                                              F Cl                                                                                  ##STR213##                                                          2.125                                                                              F Cl                                                                                  ##STR214##                                                          2.126                                                                              F Cl                                                                                  ##STR215##                                                          2.127                                                                              F Cl                                                                                  ##STR216##                                                          2.128                                                                              F Cl                                                                                  ##STR217##                                                          2.129                                                                              F Cl                                                                                  ##STR218##                                                          2.130                                                                              F Cl                                                                                  ##STR219##                                                          2.131                                                                              F Cl                                                                                  ##STR220##                                                          2.132                                                                              F Cl                                                                                  ##STR221##                                                          2.133                                                                              F Cl                                                                                  ##STR222##                                                          2.134                                                                              F Cl                                                                                  ##STR223##                                                          2.135                                                                              F Cl                                                                                  ##STR224##                                                          2.136                                                                              F Cl                                                                                  ##STR225##                                                          2.137                                                                              F Cl                                                                                  ##STR226##                                                          2.138                                                                              F Cl                                                                                  ##STR227##                                                          2.139                                                                              F Cl                                                                                  ##STR228##                                                          2.140                                                                              F Cl                                                                                  ##STR229##                                                          2.141                                                                              F Cl                                                                                  ##STR230##                                                          2.142                                                                              F Cl                                                                                  ##STR231##                                                          2.143                                                                              F Cl                                                                                  ##STR232##                                                          2.144                                                                              F Cl                                                                                  ##STR233##                                                          2.145                                                                              F Cl                                                                                  ##STR234##                                                          2.146                                                                              F Cl  NHSO.sub.2CH.sub.3                                                   2.147                                                                              F Cl  NHSO.sub.2C.sub.2 H.sub.5                                            2.148                                                                              F Cl  NHSO.sub.2Cl                                                         2.149                                                                              F Cl                                                                                  ##STR235##                                                          2.150                                                                              F Cl                                                                                  ##STR236##                                                          2.151                                                                              H Cl  COOH                                                                 2.152                                                                              H Cl  COOCH.sub.3                                                          2.153                                                                              H Cl                                                                                  ##STR237##                                                          2.154                                                                              H Cl  COOC.sub.5 H.sub.11                                                  2.155                                                                              H Cl  COOCH.sub.2CH.sub.2OCH.sub.3                                         2.156                                                                              H Cl  COOCH.sub.2SCH.sub.3                                                 2.157                                                                              H Cl  COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                     2.158                                                                              H Cl                                                                                  ##STR238##                                                          2.159                                                                              H Cl                                                                                  ##STR239##                                                          2.160                                                                              H Cl                                                                                  ##STR240##                                                          2.161                                                                              H Cl                                                                                  ##STR241##                                                          2.162                                                                              H Cl                                                                                  ##STR242##                                                          2.163                                                                              H Cl                                                                                  ##STR243##                                                          2.164                                                                              H Cl                                                                                  ##STR244##                                                          2.165                                                                              H Cl  SC.sub.3 H.sub.7                                                     2.166                                                                              H Cl  COOCH.sub.2COOCH.sub.3                                               2.167                                                                              H Cl  COOCH(CH.sub.3)COOCH.sub.3                                           2.168                                                                              H Cl  COSCH.sub.2COOCH.sub.3                                               2.169                                                                              H Cl  COSCH(CH.sub.3)COOCH.sub.3                                           2.170                                                                              H Cl  OH                                                                   2.171                                                                              H Cl  OCH.sub.3                                                            2.172                                                                              H Cl  OC.sub.2 H.sub.5                                                     2.173                                                                              H Cl                                                                                  ##STR245##                                                          2.174                                                                              H Cl  OCH.sub.2CCH                                                         2.175                                                                              H Cl  OCH.sub.2CHCHCl                                                      2.176                                                                              H Cl                                                                                  ##STR246##                                                          2.177                                                                              H Cl                                                                                  ##STR247##                                                          2.178                                                                              H Cl  OCH.sub.2COOCH.sub.3                                                 2.179                                                                              H Cl  OCH.sub.2COOC.sub.2 H.sub.5                                          2.180                                                                              H Cl  OCH(CH.sub.3)COOCH.sub.3                                             2.181                                                                              H Cl  SH                                                                   2.182                                                                              H Cl  SCH.sub.3                                                            2.183                                                                              H Cl  SC.sub.2 H.sub.5                                                     2.184                                                                              H Cl                                                                                  ##STR248##                                                          2.185                                                                              H Cl  SCH.sub.2COOCH.sub.3                                                 2.186                                                                              H Cl  SCH(CH.sub.3)COOCH.sub.3                                             2.187                                                                              H Cl  SCH.sub.2COOC.sub.2 H.sub.5                                          2.188                                                                              H Cl                                                                                  ##STR249##                                                          2.189                                                                              H Cl                                                                                  ##STR250##                                                          2.190                                                                              H Cl                                                                                  ##STR251##                                                          2.191                                                                              H Cl                                                                                  ##STR252##                                                          2.192                                                                              H Cl                                                                                  ##STR253##                                                          2.193                                                                              H Cl                                                                                  ##STR254##                                                          2.194                                                                              H Cl                                                                                  ##STR255##                                                          2.195                                                                              H Cl                                                                                  ##STR256##                                                          2.196                                                                              H Cl                                                                                  ##STR257##                                                          2.197                                                                              H Cl                                                                                  ##STR258##                                                          2.198                                                                              H Cl                                                                                  ##STR259##                                                          2.199                                                                              H Cl                                                                                  ##STR260##                                                          2.200                                                                              H Cl                                                                                  ##STR261##                                                          2.201                                                                              H Cl                                                                                  ##STR262##                                                          2.202                                                                              H Cl  NHSO.sub.2C.sub.2 H.sub.5                                            2.203                                                                              H Cl  NHSO.sub.2CH.sub.2Cl                                                 2.204                                                                              F CN  COOH                                                                 2.205                                                                              F CN                                                                                  ##STR263##                                                          2.206                                                                              F CN                                                                                  ##STR264##                                                          2.207                                                                              F CN  OCH.sub.2CCH                                                         2.208                                                                              F CN  OCH(CH.sub.3)CCH                                                     2.209                                                                              F CN  SCH.sub.2COOCH.sub.3                                                 2.210                                                                              F CN  SCH(CH.sub.3)COOCH.sub.3                                             2.211                                                                              F CN  OCH.sub.2COOCH.sub.3                                                 2.212                                                                              F CN  OCH.sub.2COOC.sub.5 H.sub.11                                         2.213                                                                              F CN  OCH(CH.sub.3)COOC.sub.2 H.sub.5                                      2.214                                                                              F CN                                                                                  ##STR265##                                                          2.215                                                                              F CN                                                                                  ##STR266##                                                          2.216                                                                              F CN                                                                                  ##STR267##                                                          2.217                                                                              F CN                                                                                  ##STR268##                                                          2.218                                                                              F CN                                                                                  ##STR269##                                                          2.219                                                                              F CN                                                                                  ##STR270##                                                          2.220                                                                              F CN                                                                                  ##STR271##                                                          2.221                                                                              F Br  COOH                                                                 2.222                                                                              F Br                                                                                  ##STR272##                                                          2.223                                                                              F Br  OH                                                                   2.224                                                                              F Br                                                                                  ##STR273##                                                          2.225                                                                              F Br  OCH.sub.2CCH                                                         2.226                                                                              F Br  OCH(CH.sub.3)CCH                                                     2.227                                                                              F Br  OCH.sub.2 COOCH.sub.3                                                2.228                                                                              F Br  OCH.sub.2COOC.sub.5 H.sub.11                                         2.229                                                                              F Br  S CH.sub.2COOCH.sub.3                                                2.230                                                                              F Br                                                                                  ##STR274##                                                          2.231                                                                              F Br                                                                                  ##STR275##                                                          2.232                                                                              F Br                                                                                  ##STR276##                                                          2.233                                                                              F Cl  SCH.sub.2 COOH                                                       __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________     Compounds of formula Ie:                                                        ##STR277##                              (Ie)                                  Comp.                                                                          No. R.sub.1                                                                          R.sub.2                                                                           A                      phys. data                                     __________________________________________________________________________     3.001                                                                              F Cl                                                                               H                                                                      3.002                                                                              F Cl                                                                               CN                                                                     3.003                                                                              F Cl                                                                               NO.sub.2                                                               3.004                                                                              F Cl                                                                               COOH                                                                   3.005                                                                              F Cl                                                                               COOCH.sub.3            m.p. 118-119° C.                         3.006                                                                              F Cl                                                                               COOC.sub.2 H.sub.5                                                     3.007                                                                              F Cl                                                                               COOC.sub.3 H.sub.7                                                     3.008                                                                              F Cl                                                                               COOCH(CH.sub.3).sub.2                                                  3.009                                                                              F Cl                                                                               COOC.sub.4 H.sub.9                                                     3.010                                                                              F Cl                                                                                ##STR278##                                                            3.011                                                                              F Cl                                                                                ##STR279##                                                            3.012                                                                              F Cl                                                                               COOC.sub.5 H.sub.11                                                    3.013                                                                              F Cl                                                                               COOCH.sub.2CH.sub.2OCH.sub.3                                           3.014                                                                              F Cl                                                                               COOCH.sub.2CH.sub.2OC.sub.2 H.sub.5                                    3.015                                                                              F Cl                                                                               COOCH(CH.sub.3)CH.sub.2OCH.sub.3                                       3.016                                                                              F Cl                                                                               COOCH.sub.2CH.sub.2SCH.sub.3                                           3.017                                                                              F Cl                                                                               COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                       3.018                                                                              F Cl                                                                               COOCH(CH.sub.3)CH.sub.2SC.sub.2 H.sub.5                                3.019                                                                              F Cl                                                                               COOCH(CH.sub.3)CH.sub.2SC.sub.3 H.sub.7                                3.020                                                                              F Cl                                                                                ##STR280##                                                            3.021                                                                              F Cl                                                                               COOCH(CH.sub.3)CH.sub.2SC.sub.4 H.sub.9                                3.022                                                                              F Cl                                                                               COOCH(CH.sub.3)CH.sub.2SC.sub.5 H.sub.11                               3.023                                                                              F Cl                                                                                ##STR281##                                                            3.024                                                                              F Cl                                                                                ##STR282##                                                            3.025                                                                              F Cl                                                                               CONH.sub.2                                                             3.026                                                                              F Cl                                                                               CONHCH.sub.3                                                           3.027                                                                              F Cl                                                                                ##STR283##                                                            3.028                                                                              F Cl                                                                                ##STR284##                                                            3.029                                                                              F Cl                                                                                ##STR285##                                                            3.030                                                                              F Cl                                                                               CONHCH.sub.2CHCH.sub.2                                                 3.031                                                                              F Cl                                                                               CON(CH.sub.2CHCH.sub.2).sub.2                                          3.032                                                                              F Cl                                                                                ##STR286##                                                            3.033                                                                              F Cl                                                                                ##STR287##                                                            3.034                                                                              F Cl                                                                                ##STR288##                                                            3.035                                                                              F Cl                                                                                ##STR289##                                                            3.036                                                                              F Cl                                                                                ##STR290##                                                            3.037                                                                              F Cl                                                                                ##STR291##                                                            3.038                                                                              F Cl                                                                               COOCH.sub.2CH.sub.2Cl                                                  3.039                                                                              F Cl                                                                               COOCH.sub.2CN                                                          3.040                                                                              F Cl                                                                                ##STR292##                                                            3.041                                                                              F Cl                                                                               COOCH.sub.2 CHCH.sub.2                                                 3.042                                                                              F Cl                                                                               COOCH.sub.2CHCHCl                                                      3.043                                                                              F Cl                                                                                ##STR293##                                                            3.044                                                                              F Cl                                                                               COOCH.sub.2CCH                                                         3.045                                                                              F Cl                                                                                ##STR294##                                                            3.046                                                                              F Cl                                                                                ##STR295##                                                            3.047                                                                              F Cl                                                                                ##STR296##                                                            3.048                                                                              F Cl                                                                                ##STR297##                                                            3.049                                                                              F Cl                                                                                ##STR298##                                                            3.050                                                                              F Cl                                                                                ##STR299##                                                            3.051                                                                              F Cl                                                                                ##STR300##                                                            3.052                                                                              F Cl                                                                                ##STR301##                                                            3.053                                                                              F Cl                                                                               COSCH.sub.3                                                            3.054                                                                              F Cl                                                                               COSC.sub.2 H.sub.5                                                     3.055                                                                              F Cl                                                                               COSC.sub.3 H.sub.7                                                     3.056                                                                              F Cl                                                                               COSCH.sub.2CHCH.sub.2                                                  3.057                                                                              F Cl                                                                               COS CH.sub.2COOCH.sub.3                                                3.058                                                                              F Cl                                                                               COSCH.sub.2COOC.sub.2 H.sub.5                                          3.059                                                                              F Cl                                                                               COSCH.sub.2COOC.sub.5 H.sub.11                                         3.060                                                                              F Cl                                                                                ##STR302##                                                            3.061                                                                              F Cl                                                                                ##STR303##                                                            3.062                                                                              F Cl                                                                                ##STR304##                                                            3.063                                                                              F Cl                                                                               COSCH.sub.2CH.sub.2COOCH.sub.3                                         3.064                                                                              F Cl                                                                               COSCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                                3.065                                                                              F Cl                                                                               COOCH.sub.2COOCH.sub.3                                                 3.066                                                                              F Cl                                                                                ##STR305##                                                            3.067                                                                              F Cl                                                                               COOCH.sub.2COOC.sub.5 H.sub.11                                         3.068                                                                              F Cl                                                                               COOCH.sub.2 CH.sub.2Si(CH.sub.3).sub.3                                 3.069                                                                              F Cl                                                                               COONa                                                                  3.070                                                                              F Cl                                                                                ##STR306##                                                            3.071                                                                              F Cl                                                                               OH                                                                     3.072                                                                              F Cl                                                                               OCH.sub.3                                                              3.073                                                                              F Cl                                                                               OC.sub.2 H.sub.5                                                       3.074                                                                              F Cl                                                                               OC.sub.3 H.sub. 7                                                      3.075                                                                              F Cl                                                                                ##STR307##            resin                                           3.076                                                                              F Cl                                                                               OC.sub.4 H.sub.9                                                       3.077                                                                              F Cl                                                                                ##STR308##                                                            3.078                                                                              F Cl                                                                                ##STR309##                                                            3.079                                                                              F Cl                                                                               OCH.sub.2 CHCH.sub.2                                                   3.080                                                                              F Cl                                                                                ##STR310##                                                            3.081                                                                              F Cl                                                                               OCH.sub.2 CHCHCl                                                       3.082                                                                              F Cl                                                                               OCH.sub.2 CCH                                                          3.083                                                                              F Cl                                                                                ##STR311##                                                            3.084                                                                              F Cl                                                                               OCH.sub.2COOCH.sub.3                                                   3.085                                                                              F Cl                                                                               OCH.sub.2COOC.sub.5 H.sub.11                                           3.086                                                                              F Cl                                                                                ##STR312##                                                            3.087                                                                              F Cl                                                                               OCH.sub.2COOC.sub.2 H.sub.5                                            3.088                                                                              F Cl                                                                                ##STR313##                                                            3.089                                                                              F Cl                                                                               OCH.sub.2CH.sub.2OCH.sub.3                                             3.090                                                                              F Cl                                                                                ##STR314##                                                            3.091                                                                              F Cl                                                                                ##STR315##                                                            3.092                                                                              F Cl                                                                                ##STR316##                                                            3.093                                                                              F Cl                                                                               OCH.sub.2CH.sub.2Cl                                                    3.094                                                                              F Cl                                                                               OCH.sub.2CN                                                            3.095                                                                              F Cl                                                                                ##STR317##                                                            3.096                                                                              F Cl                                                                               SCH.sub.3                                                              3.097                                                                              F Cl                                                                               SC.sub.2 H.sub.5                                                       3.098                                                                              F Cl                                                                               SC.sub.3 H.sub.7                                                       3.099                                                                              F Cl                                                                                ##STR318##                                                            3.100                                                                              F Cl                                                                               SCH.sub.2CHCH.sub.2                                                    3.101                                                                              F Cl                                                                                ##STR319##                                                            3.102                                                                              F Cl                                                                               SCH.sub.2CHCHCl                                                        3.103                                                                              F Cl                                                                               SCH.sub.2CCH                                                           3.104                                                                              F Cl                                                                                ##STR320##                                                            3.105                                                                              F Cl                                                                               SCH.sub.2COOCH.sub.3   m.p. 63-65° C.                           3.106                                                                              F Cl                                                                               SCH.sub.2COOC.sub.2 H.sub.5                                            3.107                                                                              F Cl                                                                               SCH.sub.2COOC.sub.5 H.sub.11                                           3.108                                                                              F Cl                                                                                ##STR321##                                                            3.109                                                                              F Cl                                                                                ##STR322##                                                            3.110                                                                              F Cl                                                                               SCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                                  3.111                                                                              F Cl                                                                                ##STR323##                                                            3.112                                                                              F Cl                                                                                ##STR324##                                                            3.113                                                                              F Cl                                                                                ##STR325##                                                            3.114                                                                              F Cl                                                                                ##STR326##                                                            3.115                                                                              F Cl                                                                                ##STR327##                                                            3.116                                                                              F Cl                                                                                ##STR328##                                                            3.117                                                                              F Cl                                                                                ##STR329##                                                            3.118                                                                              F Cl                                                                                ##STR330##                                                            3.119                                                                              F Cl                                                                                ##STR331##                                                            3.120                                                                              F Cl                                                                                ##STR332##                                                            3.121                                                                              F Cl                                                                                ##STR333##                                                            3.122                                                                              F Cl                                                                                ##STR334##                                                            3.123                                                                              F Cl                                                                                ##STR335##                                                            3.124                                                                              F Cl                                                                                ##STR336##                                                            3.125                                                                              F Cl                                                                                ##STR337##                                                            3.126                                                                              F Cl                                                                                ##STR338##                                                            3.127                                                                              F Cl                                                                                ##STR339##                                                            3.128                                                                              F Cl                                                                                ##STR340##                                                            3.129                                                                              F Cl                                                                                ##STR341##                                                            3.130                                                                              F Cl                                                                                ##STR342##                                                            3.131                                                                              F Cl                                                                                ##STR343##                                                            3.132                                                                              F Cl                                                                                ##STR344##                                                            3.133                                                                              F Cl                                                                                ##STR345##                                                            3.134                                                                              F Cl                                                                                ##STR346##                                                            3.135                                                                              F Cl                                                                                ##STR347##                                                            3.136                                                                              F Cl                                                                                ##STR348##                                                            3.137                                                                              F Cl                                                                                ##STR349##                                                            3.138                                                                              F Cl                                                                                ##STR350##                                                            3.139                                                                              F Cl                                                                                ##STR351##                                                            3.140                                                                              F Cl                                                                                ##STR352##                                                            3.141                                                                              F Cl                                                                                ##STR353##                                                            3.142                                                                              F Cl                                                                                ##STR354##                                                            3.143                                                                              F Cl                                                                                ##STR355##                                                            3.144                                                                              F Cl                                                                                ##STR356##                                                            3.145                                                                              F Cl                                                                                ##STR357##                                                            3.146                                                                              F Cl                                                                               NHSO.sub.2CH.sub.3                                                     3.147                                                                              F Cl                                                                               NHSO.sub.2C.sub.2 H.sub.5                                              3.148                                                                              F Cl                                                                               NHSO.sub.2Cl                                                           3.149                                                                              F Cl                                                                                ##STR358##                                                            3.150                                                                              F Cl                                                                                ##STR359##                                                            3.151                                                                              H Cl                                                                               COOH                                                                   3.152                                                                              H Cl                                                                               COOCH.sub.3            m.p. > 85° C. (decomp.)                  3.153                                                                              H Cl                                                                                ##STR360##            wax                                             3.154                                                                              H Cl                                                                               COOC.sub.5 H.sub.11                                                    3.155                                                                              H Cl                                                                               COOCH.sub.2CH.sub.2OCH.sub.3                                           3.156                                                                              H Cl                                                                               COOCH.sub.2SCH.sub.3                                                   3.157                                                                              H Cl                                                                               COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                       3.158                                                                              H Cl                                                                                ##STR361##                                                            3.159                                                                              H Cl                                                                                ##STR362##                                                            3.160                                                                              H Cl                                                                                ##STR363##                                                            3.161                                                                              H Cl                                                                                ##STR364##                                                            3.162                                                                              H Cl                                                                                ##STR365##                                                            3.163                                                                              H Cl                                                                                ##STR366##                                                            3.164                                                                              H Cl                                                                                ##STR367##                                                            3.165                                                                              H Cl                                                                               SC.sub.3 H.sub.7                                                       3.166                                                                              H Cl                                                                               COOCH.sub.2COOCH.sub.3                                                 3.167                                                                              H Cl                                                                               COOCH(CH.sub.3)COOCH.sub.3                                             3.168                                                                              H Cl                                                                               COSCH.sub.2COOCH.sub.3                                                 3.169                                                                              H Cl                                                                               COSCH(CH.sub.3)COOCH.sub.3                                             3.170                                                                              H Cl                                                                               OH                                                                     3.171                                                                              H Cl                                                                               OCH.sub.3                                                              3.172                                                                              H Cl                                                                               OC.sub.2 H.sub.5                                                       3.173                                                                              H Cl                                                                                ##STR368##                                                            3.174                                                                              H Cl                                                                               OCH.sub.2CCH                                                           3.175                                                                              H Cl                                                                               OCH.sub.2CHCHCl                                                        3.176                                                                              H Cl                                                                                ##STR369##                                                            3.177                                                                              H Cl                                                                                ##STR370##                                                            3.178                                                                              H Cl                                                                               OCH.sub.2COOCH.sub.3                                                   3.179                                                                              H Cl                                                                               OCH.sub.2COOC.sub.2 H.sub.5                                            3.180                                                                              H Cl                                                                               OCH(CH.sub.3)COOCH.sub.3                                               3.181                                                                              H Cl                                                                               SH                                                                     3.182                                                                              H Cl                                                                               SCH.sub.3                                                              3.183                                                                              H Cl                                                                               SC.sub.2 H.sub.5                                                       3.184                                                                              H Cl                                                                                ##STR371##                                                            3.185                                                                              H Cl                                                                               SCH.sub.2COOCH.sub.3                                                   3.186                                                                              H Cl                                                                               SCH(CH.sub.3)COOCH.sub.3                                               3.187                                                                              H Cl                                                                               SCH.sub.2COOC.sub.2 H.sub.5                                            3.188                                                                              H Cl                                                                                ##STR372##                                                            3.189                                                                              H Cl                                                                                ##STR373##                                                            3.190                                                                              H Cl                                                                                ##STR374##                                                            3.191                                                                              H Cl                                                                                ##STR375##                                                            3.192                                                                              H Cl                                                                                ##STR376##                                                            3.193                                                                              H Cl                                                                                ##STR377##                                                            3.194                                                                              H Cl                                                                                ##STR378##                                                            3.195                                                                              H Cl                                                                                ##STR379##                                                            3.196                                                                              H Cl                                                                                ##STR380##                                                            3.197                                                                              H Cl                                                                                ##STR381##                                                            3.198                                                                              H Cl                                                                                ##STR382##                                                            3.199                                                                              H Cl                                                                                ##STR383##                                                            3.200                                                                              H Cl                                                                                ##STR384##                                                            3.201                                                                              H Cl                                                                                ##STR385##                                                            3.202                                                                              H Cl                                                                               NHSO.sub.2C.sub.2 H.sub.5                                              3.203                                                                              H Cl                                                                               NHSO.sub.2CH.sub.2Cl                                                   3.204                                                                              F CN                                                                               COOH                                                                   3.205                                                                              F CN                                                                                ##STR386##                                                            3.206                                                                              F CN                                                                                ##STR387##                                                            3.207                                                                              F CN                                                                               OCH.sub.2CCH                                                           3.208                                                                              F CN                                                                               OCH(CH.sub.3)CCH                                                       3.209                                                                              F CN                                                                               SCH.sub.2COOCH.sub.3                                                   3.210                                                                              F CN                                                                               SCH(CH.sub.3)COOCH.sub.3                                               3.211                                                                              F CN                                                                               OCH.sub.2COOCH.sub.3                                                   3.212                                                                              F CN                                                                               OCH.sub.2COOC.sub.5 H.sub.11                                           3.213                                                                              F CN                                                                               OCH(CH.sub.3)COOC.sub.2 H.sub.5                                        3.214                                                                              F CN                                                                                ##STR388##                                                            3.215                                                                              F CN                                                                                ##STR389##                                                            3.216                                                                              F CN                                                                                ##STR390##                                                            3.217                                                                              F CN                                                                                ##STR391##                                                            3.218                                                                              F CN                                                                                ##STR392##                                                            3.219                                                                              F CN                                                                                ##STR393##                                                            3.220                                                                              F CN                                                                                ##STR394##                                                            3.221                                                                              F Br                                                                               COOH                                                                   3.222                                                                              F Br                                                                                ##STR395##                                                            3.223                                                                              F Br                                                                               OH                                                                     3.224                                                                              F Br                                                                                ##STR396##                                                            3.225                                                                              F Br                                                                               OCH.sub.2CCH                                                           3.226                                                                              F Br                                                                               OCH(CH.sub.3)CCH                                                       3.227                                                                              F Br                                                                               OCH.sub.2 COOCH.sub.3                                                  3.228                                                                              F Br                                                                               OCH.sub.2 COOC.sub.5 H.sub.11                                          3.229                                                                              F Br                                                                               SCH.sub.2COOCH.sub.3                                                   3.230                                                                              F Br                                                                                ##STR397##                                                            3.231                                                                              F Br                                                                                ##STR398##                                                            3.232                                                                              F Br                                                                                ##STR399##                                                            3.233                                                                              F Cl                                                                               SCH.sub.2 COOH                                                         __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________     Compounds of formula If                                                         ##STR400##                         (If)                                       Comp. No.                                                                            R.sub.1                                                                          R.sub.2                                                                           A                     phys. data                                    __________________________________________________________________________     4.001 F Cl H                                                                   4.002 F Cl CN                                                                  4.003 F Cl NO.sub.2                                                            4.004 F Cl COOH                                                                4.005 F Cl COOCH.sub.3                                                         4.006 F Cl COOC.sub.2 H.sub.5                                                  4.007 F Cl COOC.sub.3 H.sub.7                                                  4.008 F Cl COOCH(CH.sub.3).sub.2                                               4.009 F Cl COOC.sub.4 H.sub.9                                                  4.010 F Cl                                                                                 ##STR401##                                                         4.011 F Cl                                                                                 ##STR402##                                                         4.012 F Cl COOC.sub.5 H.sub.11                                                 4.013 F Cl COOCH.sub.2 CH.sub.2  OCH.sub.3                                     4.014 F Cl COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                               4.015 F Cl COOCH(CH.sub.3)CH.sub.2 OCH.sub.3                                   4.016 F Cl COOCH.sub.2 CH.sub.2 SCH.sub.3                                      4.017 F Cl COOCH(CH.sub.3)CH.sub.2 SCH.sub.3                                   4.018 F Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.2 H.sub.5                            4.019 F Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.3 H.sub.7                            4.020 F Cl                                                                                 ##STR403##                                                         4.021 F Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.4 H.sub.9                            4.022 F Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.5 H.sub.11                           4.023 F Cl                                                                                 ##STR404##                                                         4.024 F Cl                                                                                 ##STR405##                                                         4.025 F Cl CONH.sub.2                                                          4.026 F Cl CONHCH.sub.3                                                        4.027 F Cl                                                                                 ##STR406##                                                         4.028 F Cl                                                                                 ##STR407##                                                         4.029 F Cl                                                                                 ##STR408##                                                         4.030 F Cl CONHCH.sub.2 CHCH.sub.2                                             4.031 F Cl CON(CH.sub.2 CHCH.sub.2).sub.2                                      4.032 F Cl                                                                                 ##STR409##                                                         4.033 F Cl                                                                                 ##STR410##                                                         4.034 F Cl                                                                                 ##STR411##                                                         4.035 F Cl                                                                                 ##STR412##                                                         4.036 F Cl                                                                                 ##STR413##                                                         4.037 F Cl                                                                                 ##STR414##                                                         4.038 F Cl COOCH.sub.2 CH.sub.2 Cl                                             4.039 F Cl COOCH.sub.2 CN                                                      4.040 F Cl                                                                                 ##STR415##                                                         4.041 F Cl COOCH.sub.2 CHCH.sub.2                                              4.042 F Cl COOCH.sub.2 CHCHCl                                                  4.043 F Cl                                                                                 ##STR416##                                                         4.044 F Cl COOCH.sub.2 CCH                                                     4.045 F Cl                                                                                 ##STR417##                                                         4.046 F Cl                                                                                 ##STR418##                                                         4.047 F Cl                                                                                 ##STR419##                                                         4.048 F Cl                                                                                 ##STR420##                                                         4.049 F Cl                                                                                 ##STR421##                                                         4.050 F Cl                                                                                 ##STR422##                                                         4.051 F Cl                                                                                 ##STR423##                                                         4.052 F Cl                                                                                 ##STR424##                                                         4.053 F Cl COSCH.sub.3                                                         4.054 F Cl COSC.sub.2 H.sub.5                                                  4.055 F Cl COSC.sub.3 H.sub.7                                                  4.056 F Cl COSCH.sub.2 CH CH.sub.2                                             4.057 F Cl COSCH.sub.2 COOCH.sub.3                                             4.058 F Cl COSCH.sub.2 COOC.sub.2 H.sub.5                                      4.059 F Cl COSCH.sub.2 COOC.sub.5 H.sub.11                                     4.060 F Cl                                                                                 ##STR425##                                                         4.061 F Cl                                                                                 ##STR426##                                                         4.062 F Cl                                                                                 ##STR427##                                                         4.063 F Cl COSCH.sub.2 CH.sub.2 COOCH.sub.3                                    4.064 F Cl COSCH.sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                          4.065 F Cl COOCH.sub.2 COOCH.sub.3                                             4.066 F Cl                                                                                 ##STR428##                                                         4.067 F Cl COOCH.sub.2 COOC.sub.5 H.sub.11                                     4.068 F Cl COOCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                             4.069 F Cl COONa                                                               4.070 F Cl                                                                                 ##STR429##                                                         4.071 F Cl OH                                                                  4.072 F Cl OCH.sub.3                                                           4.073 F Cl OC.sub.2 H.sub.5                                                    4.074 F Cl OC.sub.3 H.sub.7                                                    4.075 F Cl                                                                                 ##STR430##                                                         4.076 F Cl OC.sub.4 H.sub.9                                                    4.077 F Cl                                                                                 ##STR431##                                                         4.078 F Cl                                                                                 ##STR432##                                                         4.079 F Cl OCH.sub.2 CHCH.sub.2                                                4.080 F Cl                                                                                 ##STR433##                                                         4.081 F Cl OCH.sub.2 CHCHCl                                                    4.082 F Cl OCH.sub.2 CCH                                                       4.083 F Cl                                                                                 ##STR434##                                                         4.084 F Cl OCH.sub.2 COOCH.sub.3                                               4.085 F Cl OCH.sub.2 COOC.sub.5 H.sub.11                                       4.086 F Cl                                                                                 ##STR435##                                                         4.087 F Cl OCH.sub.2 COOC.sub.2 H.sub.5                                        4.088 F Cl                                                                                 ##STR436##                                                         4.089 F Cl OCH.sub.2 CH.sub.2OCH.sub.3                                         4.090 F Cl                                                                                 ##STR437##                                                         4.091 F Cl                                                                                 ##STR438##                                                         4.092 F Cl                                                                                 ##STR439##                                                         4.093 F Cl OCH.sub.2CH.sub.2 Cl                                                4.094 F Cl OCH.sub.2 CN                                                        4.095 F Cl                                                                                 ##STR440##                                                         4.096 F Cl SCH.sub.3                                                           4.097 F Cl SC.sub.2 H.sub.5                                                    4.098 F Cl SC.sub.3 H.sub.7                                                    4.099 F Cl                                                                                 ##STR441##                                                         4.100 F Cl SCH.sub.2 CHCH.sub.2                                                4.101 F Cl                                                                                 ##STR442##                                                         4.102 F Cl SCH.sub.2 CHCHCl                                                    4.103 F Cl SCH.sub.2 CCH                                                       4.104 F Cl                                                                                 ##STR443##                                                         4.105 F Cl SCH.sub.2 COOCH.sub.3                                               4.106 F Cl SCH.sub.2 COOC.sub.2 H.sub.5                                        4.107 F Cl SCH.sub.2 COOC.sub.5 H.sub.11                                       4.108 F Cl                                                                                 ##STR444##                                                         4.109 F Cl                                                                                 ##STR445##                                                         4.110 F Cl SCH.sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                            4.111 F Cl                                                                                 ##STR446##                                                         4.112 F Cl                                                                                 ##STR447##                                                         4.113 F Cl                                                                                 ##STR448##                                                         4.114 F Cl                                                                                 ##STR449##                                                         4.115 F Cl                                                                                 ##STR450##                                                         4.116 F Cl                                                                                 ##STR451##                                                         4.117 F Cl                                                                                 ##STR452##                                                         4.118 F Cl                                                                                 ##STR453##                                                         4.119 F Cl                                                                                 ##STR454##                                                         4.120 F Cl                                                                                 ##STR455##                                                         4.121 F Cl                                                                                 ##STR456##                                                         4.122 F Cl                                                                                 ##STR457##                                                         4.123 F Cl                                                                                 ##STR458##                                                         4.124 F Cl                                                                                 ##STR459##                                                         4.125 F Cl                                                                                 ##STR460##                                                         4.126 F Cl                                                                                 ##STR461##                                                         4.127 F Cl                                                                                 ##STR462##                                                         4.128 F Cl                                                                                 ##STR463##                                                         4.129 F Cl                                                                                 ##STR464##                                                         4.130 F Cl                                                                                 ##STR465##                                                         4.131 F Cl                                                                                 ##STR466##                                                         4.132 F Cl                                                                                 ##STR467##                                                         4.133 F Cl                                                                                 ##STR468##                                                         4.134 F Cl                                                                                 ##STR469##                                                         4.135 F Cl                                                                                 ##STR470##                                                         4.136 F Cl                                                                                 ##STR471##                                                         4.137 F Cl                                                                                 ##STR472##                                                         4.138 F Cl                                                                                 ##STR473##                                                         4.139 F Cl                                                                                 ##STR474##                                                         4.140 F Cl                                                                                 ##STR475##                                                         4.141 F Cl                                                                                 ##STR476##                                                         4.142 F Cl                                                                                 ##STR477##                                                         4.143 F Cl                                                                                 ##STR478##                                                         4.144 F Cl                                                                                 ##STR479##                                                         4.145 F Cl                                                                                 ##STR480##                                                         4.146 F Cl NHSO.sub.2 CH.sub.3                                                 4.147 F Cl NHSO.sub.2 C.sub.2 H.sub.5                                          4.148 F Cl NHSO.sub.2 Cl                                                       4.149 F Cl                                                                                 ##STR481##                                                         4.150 F Cl                                                                                 ##STR482##                                                         4.151 H Cl COOH                                                                4.152 H Cl COOCH.sub.3                                                         4.153 H Cl                                                                                 ##STR483##                                                         4.154 H Cl COOC.sub.5 H.sub.11                                                 4.155 H Cl COOCH.sub.2CH.sub.2 OCH.sub.3                                       4.156 H Cl COOCH.sub.2 SCH.sub.3                                               4.157 H Cl COOCH(CH.sub.3)CH.sub.2 SCH.sub.3                                   4.158 H Cl                                                                                 ##STR484##                                                         4.159 H Cl                                                                                 ##STR485##                                                         4.160 H Cl                                                                                 ##STR486##                                                         4.161 H Cl                                                                                 ##STR487##                                                         4.162 H Cl                                                                                 ##STR488##                                                         4.163 H Cl                                                                                 ##STR489##                                                         4.164 H Cl                                                                                 ##STR490##                                                         4.165 H Cl SC.sub.3 H.sub.7                                                    4.166 H Cl COOCH.sub.2 COOCH.sub.3                                             4.167 H Cl COOCH(CH.sub.3)COOCH.sub.3                                          4.168 H Cl COSCH.sub.2 COOCH.sub.3                                             4.169 H Cl COSCH(CH.sub.3)COOCH.sub.3                                          4.170 H Cl OH                                                                  4.171 H Cl OCH.sub.3                                                           4.172 H Cl OC.sub.2 H.sub.5                                                    4.173 H Cl                                                                                 ##STR491##                                                         4.174 H Cl OCH.sub.2 CCH                                                       4.175 H Cl OCH.sub. 2 CHCHCl                                                   4.176 H Cl                                                                                 ##STR492##                                                         4.177 H Cl                                                                                 ##STR493##                                                         4.178 H Cl OCH.sub.2 COOCH.sub.3                                               4.179 H Cl OCH.sub.2 COOC.sub.2 H.sub.5                                        4.180 H Cl OCH(CH.sub.3)COOCH.sub.3                                            4.181 H Cl SH                                                                  4.182 H Cl SCH.sub.3                                                           4.183 H Cl SC.sub.2 H.sub.5                                                    4.184 H Cl                                                                                 ##STR494##                                                         4.185 H Cl SCH.sub.2 COOCH.sub.3                                               4.186 H Cl SCH(CH.sub.3)COOCH.sub.3                                            4.187 H Cl SCH.sub.2 COOC.sub.2 H.sub.5                                        4.188 H Cl                                                                                 ##STR495##                                                         4.189 H Cl                                                                                 ##STR496##                                                         4.190 H Cl                                                                                 ##STR497##                                                         4.191 H Cl                                                                                 ##STR498##                                                         4.192 H Cl                                                                                 ##STR499##                                                         4.193 H Cl                                                                                 ##STR500##                                                         4.194 H Cl                                                                                 ##STR501##                                                         4.195 H Cl                                                                                 ##STR502##                                                         4.196 H Cl                                                                                 ##STR503##                                                         4.197 H Cl                                                                                 ##STR504##                                                         4.198 H Cl                                                                                 ##STR505##                                                         4.199 H Cl                                                                                 ##STR506##                                                         4.200 H Cl                                                                                 ##STR507##                                                         4.201 H Cl                                                                                 ##STR508##                                                         4.202 H Cl NHSO.sub.2 C.sub.2 H.sub.5                                          4.203 H Cl NHSO.sub.2 CH.sub.2 Cl                                              4.204 F CN COOH                                                                4.205 F CN                                                                                 ##STR509##                                                         4.206 F CN                                                                                 ##STR510##                                                         4.207 F CN OCH.sub.2 CCH                                                       4.208 F CN OCH(CH.sub.3)CCH                                                    4.209 F CN SCH.sub.2 COOCH.sub.3                                               4.210 F CN SCH(CH.sub.3)COOCH.sub.3                                            4.211 F CN OCH.sub.2 COOCH.sub.3                                               4.212 F CN OCH.sub.2 COOC.sub.5 H.sub.11                                       4.213 F CN OCH(CH.sub.3)COOC.sub.2 H.sub.5                                     4.214 F CN                                                                                 ##STR511##                                                         4.215 F CN                                                                                 ##STR512##                                                         4.216 F CN                                                                                 ##STR513##                                                         4.217 F CN                                                                                 ##STR514##                                                         4.218 F CN                                                                                 ##STR515##                                                         4.219 F CN                                                                                 ##STR516##                                                         4.220 F CN                                                                                 ##STR517##                                                         4.221 F Br COOH                                                                4.222 F Br                                                                                 ##STR518##                                                         4.223 F Br OH                                                                  4.224 F Br                                                                                 ##STR519##                                                         4.225 F Br OCH.sub.2 CCH                                                       4.226 F Br OCH(CH.sub.3)CCH                                                    4.227 F Br OCH.sub.2 COOCH.sub.3                                               4.228 F Br OCH.sub.2 COOC.sub.5 H.sub.11                                       4.229 F Br SCH.sub.2 COOCH.sub.3                                               4.230 F Br                                                                                 ##STR520##                                                         4.231 F Br                                                                                 ##STR521##                                                         4.232 F Br                                                                                 ##STR522##                                                         4.233 F Cl SCH.sub.2 COOH                                                      __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________     Compounds of formula Ig                                                         ##STR523##                         (Ig)                                       Comp.                                                                          No. R.sub.1                                                                          R.sub.2                                                                            A                      phys. data                                    __________________________________________________________________________     5.001                                                                              F Cl  H                                                                    5.002                                                                              F Cl  CN                                                                   5.003                                                                              F Cl  NO.sub.2                                                             5.004                                                                              F Cl  COOH                                                                 5.005                                                                              F Cl  COOCH.sub.3                                                          5.006                                                                              F Cl  COOC.sub.2 H.sub.5                                                   5.007                                                                              F Cl  COOC.sub.3 H.sub.7                                                   5.008                                                                              F Cl  COOCH(CH.sub.3).sub.2                                                5.009                                                                              F Cl  COOC.sub.4 H.sub.9                                                   5.010                                                                              F Cl                                                                                  ##STR524##                                                          5.011                                                                              F Cl                                                                                  ##STR525##                                                          5.012                                                                              F Cl  COOC.sub.5 H.sub.11                                                  5.013                                                                              F Cl  COOCH.sub.2CH.sub.2OCH.sub.3                                         5.014                                                                              F Cl  COOCH.sub.2CH.sub.2OC.sub.2 H.sub.5                                  5.015                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2OCH.sub.3                                     5.016                                                                              F Cl  COOCH.sub.2CH.sub.2SCH.sub.3                                         5.017                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                     5.018                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.2 H.sub.5                              5.019                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.3 H.sub.7                              5.020                                                                              F Cl                                                                                  ##STR526##                                                          5.021                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.4 H.sub.9                              5.022                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.5 H.sub.11                             5.023                                                                              F Cl                                                                                  ##STR527##                                                          5.024                                                                              F Cl                                                                                  ##STR528##                                                          5.025                                                                              F Cl  CONH.sub.2                                                           5.026                                                                              F Cl  CONHCH.sub.3                                                         5.027                                                                              F Cl                                                                                  ##STR529##                                                          5.028                                                                              F Cl                                                                                  ##STR530##                                                          5.029                                                                              F Cl                                                                                  ##STR531##                                                          5.030                                                                              F Cl  CONHCH.sub.2CHCH.sub.2                                               5.031                                                                              F Cl  CON(CH.sub.2CHCH.sub.2).sub.2                                        5.032                                                                              F Cl                                                                                  ##STR532##                                                          5.033                                                                              F Cl                                                                                  ##STR533##                                                          5.034                                                                              F Cl                                                                                  ##STR534##                                                          5.035                                                                              F Cl                                                                                  ##STR535##                                                          5.036                                                                              F Cl                                                                                  ##STR536##                                                          5.037                                                                              F Cl                                                                                  ##STR537##                                                          5.038                                                                              F Cl  COOCH.sub.2CH.sub.2Cl                                                5.039                                                                              F Cl  COOCH.sub.2CN                                                        5.040                                                                              F Cl                                                                                  ##STR538##                                                          5.041                                                                              F Cl  COOCH.sub.2CHCH.sub.2                                                5.042                                                                              F Cl  COOCH.sub.2CHCHCl                                                    5.043                                                                              F Cl                                                                                  ##STR539##                                                          5.044                                                                              F Cl  COOCH.sub.2CCH                                                       5.045                                                                              F Cl                                                                                  ##STR540##                                                          5.046                                                                              F Cl                                                                                  ##STR541##                                                          5.047                                                                              F Cl                                                                                  ##STR542##                                                          5.048                                                                              F Cl                                                                                  ##STR543##                                                          5.049                                                                              F Cl                                                                                  ##STR544##                                                          5.050                                                                              F Cl                                                                                  ##STR545##                                                          5.051                                                                              F Cl                                                                                  ##STR546##                                                          5.052                                                                              F Cl                                                                                  ##STR547##                                                          5.053                                                                              F Cl  COSCH.sub.3                                                          5.054                                                                              F Cl  COSC.sub.2 H.sub.5                                                   5.055                                                                              F Cl  COSC.sub.3 H.sub.7                                                   5.056                                                                              F Cl  COSCH.sub.2CHCH.sub.2                                                5.057                                                                              F Cl  COSCH.sub.2COOCH.sub. 3                                              5.058                                                                              F Cl  COSCH.sub.2COOC.sub.2 H.sub.5                                        5.059                                                                              F Cl  COSCH.sub.2COOC.sub.5 H.sub.11                                       5.060                                                                              F Cl                                                                                  ##STR548##                                                          5.061                                                                              F Cl                                                                                  ##STR549##                                                          5.062                                                                              F Cl                                                                                  ##STR550##                                                          5.063                                                                              F Cl  COSCH.sub.2CH.sub.2COOCH.sub.3                                       5.064                                                                              F Cl  COSCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                              5.065                                                                              F Cl  COOCH.sub.2COOCH.sub.3                                               5.066                                                                              F Cl                                                                                  ##STR551##                                                          5.067                                                                              F Cl  COOCH.sub.2COOC.sub.5 H.sub.11                                       5.068                                                                              F Cl  COOCH.sub.2CH.sub.2Si(CH.sub.3).sub.3                                5.069                                                                              F Cl  COONa                                                                5.070                                                                              F Cl                                                                                  ##STR552##                                                          5.071                                                                              F Cl  OH                                                                   5.072                                                                              F Cl  OCH.sub.3                                                            5.073                                                                              F Cl  OC.sub.2 H.sub.5                                                     5.074                                                                              F Cl  OC.sub.3 H.sub.7                                                     5.075                                                                              F Cl                                                                                  ##STR553##            oil                                           5.076                                                                              F Cl  OC.sub.4 H.sub.9                                                     5.077                                                                              F Cl                                                                                  ##STR554##                                                          5.078                                                                              F Cl                                                                                  ##STR555##                                                          5.079                                                                              F Cl  OCH.sub.2 CHCH.sub.2                                                 5.080                                                                              F Cl                                                                                  ##STR556##                                                          5.081                                                                              F Cl  OCH.sub.2 CHCHCl                                                     5.082                                                                              F Cl  OCH.sub.2 CCH                                                        5.083                                                                              F Cl                                                                                  ##STR557##                                                          5.084                                                                              F Cl  OCH.sub.2COOCH.sub.3                                                 5.085                                                                              F Cl  OCH.sub.2COOC.sub.5 H.sub.11                                         5.086                                                                              F Cl                                                                                  ##STR558##                                                          5.087                                                                              F Cl  OCH.sub.2COOC.sub.2 H.sub.5                                          5.088                                                                              F Cl                                                                                  ##STR559##                                                          5.089                                                                              F Cl  OCH.sub.2CH.sub. 2OCH.sub.3                                          5.090                                                                              F Cl                                                                                  ##STR560##                                                          5.091                                                                              F Cl                                                                                  ##STR561##                                                          5.092                                                                              F Cl                                                                                  ##STR562##                                                          5.093                                                                              F Cl  OCH.sub.2CH.sub.2Cl                                                  5.094                                                                              F Cl  OCH.sub.2CN                                                          5.095                                                                              F Cl                                                                                  ##STR563##                                                          5.096                                                                              F Cl  SCH.sub.3                                                            5.097                                                                              F Cl  SC.sub.2 H.sub.5                                                     5.098                                                                              F Cl  SC.sub.3 H.sub.7                                                     5.099                                                                              F Cl                                                                                  ##STR564##                                                          5.100                                                                              F Cl  SCH.sub.2CHCH.sub.2                                                  5.101                                                                              F Cl                                                                                  ##STR565##                                                          5.102                                                                              F Cl  SCH.sub.2CHCHCl                                                      5.103                                                                              F Cl  SCH.sub.2CCH                                                         5.104                                                                              F Cl                                                                                  ##STR566##                                                          5.105                                                                              F Cl  SCH.sub.2COOCH.sub.3   oil                                           5.106                                                                              F Cl  SCH.sub.2COOC.sub.2 H.sub.5                                          5.107                                                                              F Cl  SCH.sub.2COOC.sub.5 H.sub.11                                         5.108                                                                              F Cl                                                                                  ##STR567##                                                          5.109                                                                              F Cl                                                                                  ##STR568##                                                          5.110                                                                              F Cl  SCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                                5.111                                                                              F Cl                                                                                  ##STR569##                                                          5.112                                                                              F Cl                                                                                  ##STR570##                                                          5.113                                                                              F Cl                                                                                  ##STR571##                                                          5.114                                                                              F Cl                                                                                  ##STR572##                                                          5.115                                                                              F Cl                                                                                  ##STR573##                                                          5.116                                                                              F Cl                                                                                  ##STR574##                                                          5.117                                                                              F Cl                                                                                  ##STR575##                                                          5.118                                                                              F Cl                                                                                  ##STR576##                                                          5.119                                                                              F Cl                                                                                  ##STR577##                                                          5.120                                                                              F Cl                                                                                  ##STR578##                                                          5.121                                                                              F Cl                                                                                  ##STR579##                                                          5.122                                                                              F Cl                                                                                  ##STR580##                                                          5.123                                                                              F Cl                                                                                  ##STR581##                                                          5.124                                                                              F Cl                                                                                  ##STR582##                                                          5.125                                                                              F Cl                                                                                  ##STR583##                                                          5.126                                                                              F Cl                                                                                  ##STR584##                                                          5.127                                                                              F Cl                                                                                  ##STR585##                                                          5.128                                                                              F Cl                                                                                  ##STR586##                                                          5.129                                                                              F Cl                                                                                  ##STR587##                                                          5.130                                                                              F Cl                                                                                  ##STR588##                                                          5.131                                                                              F Cl                                                                                  ##STR589##                                                          5.132                                                                              F Cl                                                                                  ##STR590##                                                          5.133                                                                              F Cl                                                                                  ##STR591##                                                          5.134                                                                              F Cl                                                                                  ##STR592##                                                          5.135                                                                              F Cl                                                                                  ##STR593##                                                          5.136                                                                              F Cl                                                                                  ##STR594##                                                          5.137                                                                              F Cl                                                                                  ##STR595##                                                          5.138                                                                              F Cl                                                                                  ##STR596##                                                          5.139                                                                              F Cl                                                                                  ##STR597##                                                          5.140                                                                              F Cl                                                                                  ##STR598##                                                          5.141                                                                              F Cl                                                                                  ##STR599##                                                          5.142                                                                              F Cl                                                                                  ##STR600##                                                          5.143                                                                              F Cl                                                                                  ##STR601##                                                          5.144                                                                              F Cl                                                                                  ##STR602##                                                          5.145                                                                              F Cl                                                                                  ##STR603##                                                          5.146                                                                              F Cl  NHSO.sub.2CH.sub.3                                                   5.147                                                                              F Cl  NHSO.sub.2C.sub.2 H.sub.5                                            5.148                                                                              F Cl  NHSO.sub.2Cl                                                         5.149                                                                              F Cl                                                                                  ##STR604##                                                          5.150                                                                              F Cl                                                                                  ##STR605##                                                          5.151                                                                              H Cl  COOH                                                                 5.152                                                                              H Cl  COOCH.sub.3                                                          5.153                                                                              H Cl                                                                                  ##STR606##            resin                                         5.154                                                                              H Cl  COOC.sub.5 H.sub.11                                                  5.155                                                                              H Cl  COOCH.sub.2CH.sub.2OCH.sub.3                                         5.156                                                                              H Cl  COOCH.sub.2SCH.sub.3                                                 5.157                                                                              H Cl  COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                     5.158                                                                              H Cl                                                                                  ##STR607##                                                          5.159                                                                              H Cl                                                                                  ##STR608##                                                          5.160                                                                              H Cl                                                                                  ##STR609##                                                          5.161                                                                              H Cl                                                                                  ##STR610##                                                          5.162                                                                              H Cl                                                                                  ##STR611##                                                          5.163                                                                              H Cl                                                                                  ##STR612##                                                          5.164                                                                              H Cl                                                                                  ##STR613##                                                          5.165                                                                              H Cl  SC.sub.3 H.sub.7                                                     5.166                                                                              H Cl  COOCH.sub.2COOCH.sub.3                                               5.167                                                                              H Cl  COOCH(CH.sub.3)COOCH.sub.3                                           5.168                                                                              H Cl  COSCH.sub.2COOCH.sub.3                                               5.169                                                                              H Cl  COSCH(CH.sub.3)COOCH.sub.3                                           5.170                                                                              H Cl  OH                                                                   5.171                                                                              H Cl  OCH.sub.3                                                            5.172                                                                              H Cl  OC.sub.2 H.sub.5                                                     5.173                                                                              H Cl                                                                                  ##STR614##                                                          5.174                                                                              H Cl  OCH.sub.2CCH                                                         5.175                                                                              H Cl  OCH.sub.2CHCHCl                                                      5.176                                                                              H Cl                                                                                  ##STR615##                                                          5.177                                                                              H Cl                                                                                  ##STR616##                                                          5.178                                                                              H Cl  OCH.sub.2COOCH.sub.3                                                 5.179                                                                              H Cl  OCH.sub.2COOC.sub.2 H.sub.5                                          5.180                                                                              H Cl  OCH(CH.sub.3)COOCH.sub.3                                             5.181                                                                              H Cl  SH                                                                   5.182                                                                              H Cl  SCH.sub.3                                                            5.183                                                                              H Cl  SC.sub.2 H.sub.5                                                     5.184                                                                              H Cl                                                                                  ##STR617##                                                          5.185                                                                              H Cl  SCH.sub.2COOCH.sub.3                                                 5.186                                                                              H Cl  SCH(CH.sub.3)COOCH.sub.3                                             5.187                                                                              H Cl  SCH.sub.2COOC.sub.2 H.sub.5                                          5.188                                                                              H Cl                                                                                  ##STR618##                                                          5.189                                                                              H Cl                                                                                  ##STR619##                                                          5.190                                                                              H Cl                                                                                  ##STR620##                                                          5.191                                                                              H Cl                                                                                  ##STR621##                                                          5.192                                                                              H Cl                                                                                  ##STR622##                                                          5.193                                                                              H Cl                                                                                  ##STR623##                                                          5.194                                                                              H Cl                                                                                  ##STR624##                                                          5.195                                                                              H Cl                                                                                  ##STR625##                                                          5.196                                                                              H Cl                                                                                  ##STR626##                                                          5.197                                                                              H Cl                                                                                  ##STR627##                                                          5.198                                                                              H Cl                                                                                  ##STR628##                                                          5.199                                                                              H Cl                                                                                  ##STR629##                                                          5.200                                                                              H Cl                                                                                  ##STR630##                                                          5.201                                                                              H Cl                                                                                  ##STR631##                                                          5.202                                                                              H Cl  NHSO.sub.2C.sub.2 H.sub.5                                            5.203                                                                              H Cl  NHSO.sub.2CH.sub.2Cl                                                 5.204                                                                              F CN  COOH                                                                 5.205                                                                              F CN                                                                                  ##STR632##                                                          5.206                                                                              F CN                                                                                  ##STR633##                                                          5.207                                                                              F CN  OCH.sub.2CCH                                                         5.208                                                                              F CN  OCH(CH.sub.3)CCH                                                     5.209                                                                              F CN  SCH.sub.2COOCH.sub.3                                                 5.210                                                                              F CN  SCH(CH.sub.3)COOCH.sub.3                                             5.211                                                                              F CN  OCH.sub.2COOCH.sub.3                                                 5.212                                                                              F CN  OCH.sub.2COOC.sub.5 H.sub.11                                         5.213                                                                              F CN  OCH(CH.sub.3)COOC.sub.2 H.sub.5                                      5.214                                                                              F CN                                                                                  ##STR634##                                                          5.215                                                                              F CN                                                                                  ##STR635##                                                          5.216                                                                              F CN                                                                                  ##STR636##                                                          5.217                                                                              F CN                                                                                  ##STR637##                                                          5.218                                                                              F CN                                                                                  ##STR638##                                                          5.219                                                                              F CN                                                                                  ##STR639##                                                          5.220                                                                              F CN                                                                                  ##STR640##                                                          5.221                                                                              F Br  COOH                                                                 5.222                                                                              F Br                                                                                  ##STR641##                                                          5.223                                                                              F Br  OH                                                                   5.224                                                                              F Br                                                                                  ##STR642##                                                          5.225                                                                              F Br  OCH.sub.2CCH                                                         5.226                                                                              F Br  OCH(CH.sub.3)CCH                                                     5.227                                                                              F Br  OCH.sub.2 COOCH.sub.3                                                5.228                                                                              F Br  OCH.sub.2COOC.sub.5 H.sub.11                                         5.229                                                                              F Br  SCH.sub.2COOCH.sub.3                                                 5.230                                                                              F Br                                                                                  ##STR643##                                                          5.231                                                                              F Br                                                                                  ##STR644##                                                          5.232                                                                              F Br                                                                                  ##STR645##                                                          5.233                                                                              F Cl  SCH.sub.2 COOH                                                       __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________     Compounds of formula Ih                                                         ##STR646##                         (Ih)                                       Comp.                                                                          No. R.sub.1                                                                          R.sub.2                                                                            A                      phys. data                                    __________________________________________________________________________     6.001                                                                              F Cl  H                                                                    6.002                                                                              F Cl  CN                                                                   6.003                                                                              F Cl  NO.sub.2                                                             6.004                                                                              F Cl  COOH                                                                 6.005                                                                              F Cl  COOCH.sub.3                                                          6.006                                                                              F Cl  COOC.sub.2 H.sub.5                                                   6.007                                                                              F Cl  COOC.sub.3 H.sub.7                                                   6.008                                                                              F Cl  COOCH(CH.sub.3).sub.2                                                6.009                                                                              F Cl  COOC.sub.4 H.sub.9                                                   6.010                                                                              F Cl                                                                                  ##STR647##                                                          6.011                                                                              F Cl                                                                                  ##STR648##                                                          6.012                                                                              F Cl  COOC.sub.5 H.sub.11                                                  6.013                                                                              F Cl  COOCH.sub.2CH.sub.2OCH.sub.3                                         6.014                                                                              F Cl  COOCH.sub.2CH.sub.2OC.sub.2 H.sub.5                                  6.015                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2OCH.sub.3                                     6.016                                                                              F Cl  COOCH.sub.2CH.sub.2SCH.sub.3                                         6.017                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                     6.018                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.2 H.sub.5                              6.019                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.3 H.sub.7                              6.020                                                                              F Cl                                                                                  ##STR649##                                                          6.021                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.4 H.sub.9                              6.022                                                                              F Cl  COOCH(CH.sub.3)CH.sub.2SC.sub.5 H.sub.11                             6.023                                                                              F Cl                                                                                  ##STR650##                                                          6.024                                                                              F Cl                                                                                  ##STR651##                                                          6.025                                                                              F Cl  CONH.sub.2                                                           6.026                                                                              F Cl  CONHCH.sub.3                                                         6.027                                                                              F Cl                                                                                  ##STR652##                                                          6.028                                                                              F Cl                                                                                  ##STR653##                                                          6.029                                                                              F Cl                                                                                  ##STR654##                                                          6.030                                                                              F Cl  CONHCH.sub.2CHCH.sub.2                                               6.031                                                                              F Cl  CON(CH.sub.2CHCH.sub.2).sub.2                                        6.032                                                                              F Cl                                                                                  ##STR655##                                                          6.033                                                                              F Cl                                                                                  ##STR656##                                                          6.034                                                                              F Cl                                                                                  ##STR657##                                                          6.035                                                                              F Cl                                                                                  ##STR658##                                                          6.036                                                                              F Cl                                                                                  ##STR659##                                                          6.037                                                                              F Cl                                                                                  ##STR660##                                                          6.038                                                                              F Cl  COOCH.sub.2CH.sub.2Cl                                                6.039                                                                              F Cl  COOCH.sub.2CN                                                        6.040                                                                              F Cl                                                                                  ##STR661##                                                          6.041                                                                              F Cl  COOCH.sub.2CHCH.sub.2                                                6.042                                                                              F Cl  COOCH.sub.2CHCHCl                                                    6.043                                                                              F Cl                                                                                  ##STR662##                                                          6.044                                                                              F Cl  COOCH.sub.2CCH                                                       6.045                                                                              F Cl                                                                                  ##STR663##                                                          6.046                                                                              F Cl                                                                                  ##STR664##                                                          6.047                                                                              F Cl                                                                                  ##STR665##                                                          6.048                                                                              F Cl                                                                                  ##STR666##                                                          6.049                                                                              F Cl                                                                                  ##STR667##                                                          6.050                                                                              F Cl                                                                                  ##STR668##                                                          6.051                                                                              F Cl                                                                                  ##STR669##                                                          6.052                                                                              F Cl                                                                                  ##STR670##                                                          6.053                                                                              F Cl  COSCH.sub.3                                                          6.054                                                                              F Cl  COSC.sub.2 H.sub.5                                                   6.055                                                                              F Cl  COSC.sub.3 H.sub.7                                                   6.056                                                                              F Cl  COSCH.sub.2CHCH.sub.2                                                6.057                                                                              F Cl  COSCH.sub.2COOCH.sub.3                                               6.058                                                                              F Cl  COSCH.sub.2COOC.sub.2 H.sub.5                                        6.059                                                                              F Cl  COSCH.sub.2COOC.sub.5 H.sub.11                                       6.060                                                                              F Cl                                                                                  ##STR671##                                                          6.061                                                                              F Cl                                                                                  ##STR672##                                                          6.062                                                                              F Cl                                                                                  ##STR673##                                                          6.063                                                                              F Cl  COSCH.sub.2CH.sub.2COOCH.sub.3                                       6.064                                                                              F Cl  COSCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                              6.065                                                                              F Cl  COOCH.sub.2COOCH.sub.3                                               6.066                                                                              F Cl                                                                                  ##STR674##                                                          6.067                                                                              F Cl  COOCH.sub.2COOC.sub.5 H.sub.11                                       6.068                                                                              F Cl  COOCH.sub.2CH.sub.2Si(CH.sub.3).sub.3                                6.069                                                                              F Cl  COONa                                                                6.070                                                                              F Cl                                                                                  ##STR675##                                                          6.071                                                                              F Cl  OH                                                                   6.072                                                                              F Cl  OCH.sub.3                                                            6.073                                                                              F Cl  OC.sub.2 H.sub.5                                                     6.074                                                                              F Cl  OC.sub.3 H.sub.7                                                     6.075                                                                              F Cl                                                                                  ##STR676##            resin                                         6.076                                                                              F Cl  OC.sub.4 H.sub.9                                                     6.077                                                                              F Cl                                                                                  ##STR677##                                                          6.078                                                                              F Cl                                                                                  ##STR678##                                                          6.079                                                                              F Cl  OCH.sub.2 CHCH.sub.2                                                 6.080                                                                              F Cl                                                                                  ##STR679##                                                          6.081                                                                              F Cl  OCH.sub.2 CHCHCl                                                     6.082                                                                              F Cl  OCH.sub.2 CCH                                                        6.083                                                                              F Cl                                                                                  ##STR680##                                                          6.084                                                                              F Cl  OCH.sub.2COOCH.sub.3                                                 6.085                                                                              F Cl  OCH.sub.2COOC.sub.5 H.sub.11                                         6.086                                                                              F Cl                                                                                  ##STR681##                                                          6.087                                                                              F Cl  OCH.sub.2COOC.sub.2 H.sub.5                                          6.088                                                                              F Cl                                                                                  ##STR682##                                                          6.089                                                                              F Cl  OCH.sub.2CH.sub.2OCH.sub.3                                           6.090                                                                              F Cl                                                                                  ##STR683##                                                          6.091                                                                              F Cl                                                                                  ##STR684##                                                          6.092                                                                              F Cl                                                                                  ##STR685##                                                          6.093                                                                              F Cl  OCH.sub.2CH.sub.2Cl                                                  6.094                                                                              F Cl  OCH.sub.2CN                                                          6.095                                                                              F Cl                                                                                  ##STR686##                                                          6.096                                                                              F Cl  SCH.sub.3                                                            6.097                                                                              F Cl  SC.sub.2 H.sub.5                                                     6.098                                                                              F Cl  SC.sub.3 H.sub.7                                                     6.099                                                                              F Cl                                                                                  ##STR687##                                                          6.100                                                                              F Cl  SCH.sub.2CHCH.sub.2                                                  6.101                                                                              F Cl                                                                                  ##STR688##                                                          6.102                                                                              F Cl  SCH.sub.2CHCHCl                                                      6.103                                                                              F Cl  SCH.sub.2CCH                                                         6.104                                                                              F Cl                                                                                  ##STR689##                                                          6.105                                                                              F Cl  SCH.sub.2COOCH.sub.3                                                 6.106                                                                              F Cl  SCH.sub.2COOC.sub.2 H.sub.5                                          6.107                                                                              F Cl  SCH.sub.2COOC.sub.5 H.sub.11                                         6.108                                                                              F Cl                                                                                  ##STR690##                                                          6.109                                                                              F Cl                                                                                  ##STR691##                                                          6.110                                                                              F Cl  SCH.sub.2COOCH.sub.2CH.sub.2OCH.sub.3                                6.111                                                                              F Cl                                                                                  ##STR692##                                                          6.112                                                                              F Cl                                                                                  ##STR693##                                                          6.113                                                                              F Cl                                                                                  ##STR694##                                                          6.114                                                                              F Cl                                                                                  ##STR695##                                                          6.115                                                                              F Cl                                                                                  ##STR696##                                                          6.116                                                                              F Cl                                                                                  ##STR697##                                                          6.117                                                                              F Cl                                                                                  ##STR698##                                                          6.118                                                                              F Cl                                                                                  ##STR699##                                                          6.119                                                                              F Cl                                                                                  ##STR700##                                                          6.120                                                                              F Cl                                                                                  ##STR701##                                                          6.121                                                                              F Cl                                                                                  ##STR702##                                                          6.122                                                                              F Cl                                                                                  ##STR703##                                                          6.123                                                                              F Cl                                                                                  ##STR704##                                                          6.124                                                                              F Cl                                                                                  ##STR705##                                                          6.125                                                                              F Cl                                                                                  ##STR706##                                                          6.126                                                                              F Cl                                                                                  ##STR707##                                                          6.127                                                                              F Cl                                                                                  ##STR708##                                                          6.128                                                                              F Cl                                                                                  ##STR709##                                                          6.129                                                                              F Cl                                                                                  ##STR710##                                                          6.130                                                                              F Cl                                                                                  ##STR711##                                                          6.131                                                                              F Cl                                                                                  ##STR712##                                                          6.132                                                                              F Cl                                                                                  ##STR713##                                                          6.133                                                                              F Cl                                                                                  ##STR714##                                                          6.134                                                                              F Cl                                                                                  ##STR715##                                                          6.135                                                                              F Cl                                                                                  ##STR716##                                                          6.136                                                                              F Cl                                                                                  ##STR717##                                                          6.137                                                                              F Cl                                                                                  ##STR718##                                                          6.138                                                                              F Cl                                                                                  ##STR719##                                                          6.139                                                                              F Cl                                                                                  ##STR720##                                                          6.140                                                                              F Cl                                                                                  ##STR721##                                                          6.141                                                                              F Cl                                                                                  ##STR722##                                                          6.142                                                                              F Cl                                                                                  ##STR723##                                                          6.143                                                                              F Cl                                                                                  ##STR724##                                                          6.144                                                                              F Cl                                                                                  ##STR725##                                                          6.145                                                                              F Cl                                                                                  ##STR726##                                                          6.146                                                                              F Cl  NHSO.sub.2CH.sub.3                                                   6.147                                                                              F Cl  NHSO.sub.2C.sub.2 H.sub.5                                            6.148                                                                              F Cl  NHSO.sub.2Cl                                                         6.149                                                                              F Cl                                                                                  ##STR727##                                                          6.150                                                                              F Cl                                                                                  ##STR728##                                                          6.151                                                                              H Cl  COOH                                                                 6.152                                                                              H Cl  COOCH.sub.3                                                          6.153                                                                              H Cl                                                                                  ##STR729##                                                          6.154                                                                              H Cl  COOC.sub.5 H.sub.11                                                  6.155                                                                              H Cl  COOCH.sub.2CH.sub.2OCH.sub.3                                         6.156                                                                              H Cl  COOCH.sub.2SCH.sub.3                                                 6.157                                                                              H Cl  COOCH(CH.sub.3)CH.sub.2SCH.sub.3                                     6.158                                                                              H Cl                                                                                  ##STR730##                                                          6.159                                                                              H Cl                                                                                  ##STR731##                                                          6.160                                                                              H Cl                                                                                  ##STR732##                                                          6.161                                                                              H Cl                                                                                  ##STR733##                                                          6.162                                                                              H Cl                                                                                  ##STR734##                                                          6.163                                                                              H Cl                                                                                  ##STR735##                                                          6.164                                                                              H Cl                                                                                  ##STR736##                                                          6.165                                                                              H Cl  SC.sub.3 H.sub.7                                                     6.166                                                                              H Cl  COOCH.sub.2COOCH.sub.3                                               6.167                                                                              H Cl  COOCH(CH.sub.3)COOCH.sub.3                                           6.168                                                                              H Cl  COSCH.sub.2COOCH.sub.3                                               6.169                                                                              H Cl  COSCH(CH.sub.3)COOCH.sub.3                                           6.170                                                                              H Cl  OH                                                                   6.171                                                                              H Cl  OCH.sub.3                                                            6.172                                                                              H Cl  OC.sub.2 H.sub.5                                                     6.173                                                                              H Cl                                                                                  ##STR737##                                                          6.174                                                                              H Cl  OCH.sub.2CCH                                                         6.175                                                                              H Cl  OCH.sub.2CHCHCl                                                      6.176                                                                              H Cl                                                                                  ##STR738##                                                          6.177                                                                              H Cl                                                                                  ##STR739##                                                          6.178                                                                              H Cl  OCH.sub.2COOCH.sub.3                                                 6.179                                                                              H Cl  OCH.sub.2COOC.sub.2 H.sub.5                                          6.180                                                                              H Cl  OCH(CH.sub.3)COOCH.sub.3                                             6.181                                                                              H Cl  SH                                                                   6.182                                                                              H Cl  SCH.sub.3                                                            6.183                                                                              H Cl  SC.sub.2 H.sub.5                                                     6.184                                                                              H Cl                                                                                  ##STR740##                                                          6.185                                                                              H Cl  SCH.sub.2COOCH.sub.3                                                 6.186                                                                              H Cl  SCH(CH.sub.3)COOCH.sub.3                                             6.187                                                                              H Cl  SCH.sub.2COOC.sub.2 H.sub.5                                          6.188                                                                              H Cl                                                                                  ##STR741##                                                          6.189                                                                              H Cl                                                                                  ##STR742##                                                          6.190                                                                              H Cl                                                                                  ##STR743##                                                          6.191                                                                              H Cl                                                                                  ##STR744##                                                          6.192                                                                              H Cl                                                                                  ##STR745##                                                          6.193                                                                              H Cl                                                                                  ##STR746##                                                          6.194                                                                              H Cl                                                                                  ##STR747##                                                          6.195                                                                              H Cl                                                                                  ##STR748##                                                          6.196                                                                              H Cl                                                                                  ##STR749##                                                          6.197                                                                              H Cl                                                                                  ##STR750##                                                          6.198                                                                              H Cl                                                                                  ##STR751##                                                          6.199                                                                              H Cl                                                                                  ##STR752##                                                          6.200                                                                              H Cl                                                                                  ##STR753##                                                          6.201                                                                              H Cl                                                                                  ##STR754##                                                          6.202                                                                              H Cl  NHSO.sub.2C.sub.2 H.sub.5                                            6.203                                                                              H Cl  NHSO.sub.2CH.sub.2Cl                                                 6.204                                                                              F CN  COOH                                                                 6.205                                                                              F CN                                                                                  ##STR755##                                                          6.206                                                                              F CN                                                                                  ##STR756##                                                          6.207                                                                              F CN  OCH.sub.2CCH                                                         6.208                                                                              F CN  OCH(CH.sub.3)CCH                                                     6.209                                                                              F CN  SCH.sub.2COOCH.sub.3                                                 6.210                                                                              F CN  SCH(CH.sub.3)COOCH.sub.3                                             6.211                                                                              F CN  OCH.sub.2COOCH.sub.3                                                 6.212                                                                              F CN  OCH.sub.2COOC.sub.5 H.sub.11                                         6.213                                                                              F CN  OCH(CH.sub.3)COOC.sub.2 H.sub.5                                      6.214                                                                              F CN                                                                                  ##STR757##                                                          6.215                                                                              F CN                                                                                  ##STR758##                                                          6.216                                                                              F CN                                                                                  ##STR759##                                                          6.217                                                                              F CN                                                                                  ##STR760##                                                          6.218                                                                              F CN                                                                                  ##STR761##                                                          6.219                                                                              F CN                                                                                  ##STR762##                                                          6.220                                                                              F CN                                                                                  ##STR763##                                                          6.221                                                                              F Br  COOH                                                                 6.222                                                                              F Br                                                                                  ##STR764##                                                          6.223                                                                              F Br  OH                                                                   6.224                                                                              F Br                                                                                  ##STR765##                                                          6.225                                                                              F Br  OCH.sub.2CCH                                                         6.226                                                                              F Br  OCH(CH.sub.3)CCH                                                     6.227                                                                              F Br  OCH.sub.2 COOCH.sub.3                                                6.228                                                                              F Br  OCH.sub.2COOC.sub.5 H.sub.11                                         6.229                                                                              F Br  SCH.sub.2COOCH.sub.3                                                 6.230                                                                              F Br                                                                                  ##STR766##                                                          6.231                                                                              F Br                                                                                  ##STR767##                                                          6.232                                                                              F Br                                                                                  ##STR768##                                                          6.233                                                                              F Cl  SCH.sub.2 COOH                                                       __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________     Compounds of formula Ii                                                         ##STR769##                         (Ii)                                       Comp.                                                                          No. R.sub.1                                                                           R.sub.2                                                                           A                      phys. data                                    __________________________________________________________________________     7.001                                                                              F  Cl H                                                                    7.002                                                                              F  Cl CN                                                                   7.003                                                                              F  Cl NO.sub.2                                                             7.004                                                                              F  Cl COOH                                                                 7.005                                                                              F  Cl COOCH.sub.3                                                          7.006                                                                              F  Cl COOC.sub.2 H.sub.5                                                   7.007                                                                              F  Cl COOC.sub.3 H.sub.7                                                   7.008                                                                              F  Cl COOCH(CH.sub.3).sub.2                                                7.009                                                                              F  Cl COOC.sub.4 H.sub.9                                                   7.010                                                                              F  Cl                                                                                 ##STR770##                                                          7.011                                                                              F  Cl                                                                                 ##STR771##                                                          7.012                                                                              F  Cl COOC.sub.5 H.sub.11                                                  7.013                                                                              F  Cl COOCH.sub.2 CH.sub.2 OCH.sub.3                                       7.014                                                                              F  Cl COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                7.015                                                                              F  Cl COOCH(CH.sub.3)CH.sub.2 OCH.sub.3                                    7.016                                                                              F  Cl COOCH.sub.2 CH.sub.2 SCH.sub.3                                       7.017                                                                              F  Cl COOCH(CH.sub.3)CH.sub.2 SCH.sub.3                                    7.018                                                                              F  Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.2 H.sub.5                             7.019                                                                              F  Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.3 H.sub.7                             7.020                                                                              F  Cl                                                                                 ##STR772##                                                          7.021                                                                              F  Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.4 H.sub.9                             7.022                                                                              F  Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.5 H.sub.11                            7.023                                                                              F  Cl                                                                                 ##STR773##                                                          7.024                                                                              F  Cl                                                                                 ##STR774##                                                          7.025                                                                              F  Cl CONH.sub.2                                                           7.026                                                                              F  Cl CONHCH.sub. 3                                                        7.027                                                                              F  Cl                                                                                 ##STR775##                                                          7.028                                                                              F  Cl                                                                                 ##STR776##                                                          7.029                                                                              F  Cl                                                                                 ##STR777##                                                          7.030                                                                              F  Cl CONHCH.sub.2 CHCH.sub.2                                              7.031                                                                              F  Cl CON(CH.sub.2 CHCH.sub.2).sub.2                                       7.032                                                                              F  Cl                                                                                 ##STR778##                                                          7.033                                                                              F  Cl                                                                                 ##STR779##                                                          7.034                                                                              F  Cl                                                                                 ##STR780##                                                          7.035                                                                              F  Cl                                                                                 ##STR781##                                                          7.036                                                                              F  Cl                                                                                 ##STR782##                                                          7.037                                                                              F  Cl                                                                                 ##STR783##                                                          7.038                                                                              F  Cl COOCH.sub.2CH.sub.2 Cl                                               7.039                                                                              F  Cl COOCH.sub.2 CN                                                       7.040                                                                              F  Cl                                                                                 ##STR784##                                                          7.041                                                                              F  Cl COOCH.sub.2 CHCH.sub.2                                               7.042                                                                              F  Cl COOCH.sub.2 CHCHCI                                                   7.043                                                                              F  Cl                                                                                 ##STR785##                                                          7.044                                                                              F  Cl COOCH.sub.2 CCH                                                      7.045                                                                              F  Cl                                                                                 ##STR786##                                                          7.046                                                                              F  Cl                                                                                 ##STR787##                                                          7.047                                                                              F  Cl                                                                                 ##STR788##                                                          7.048                                                                              F  Cl                                                                                 ##STR789##                                                          7.049                                                                              F  Cl                                                                                 ##STR790##                                                          7.050                                                                              F  Cl                                                                                 ##STR791##                                                          7.051                                                                              F  Cl                                                                                 ##STR792##                                                          7.052                                                                              F  Cl                                                                                 ##STR793##                                                          7.053                                                                              F  Cl COSCH.sub.3                                                          7.054                                                                              F  Cl COSC.sub.2 H.sub.5                                                   7.055                                                                              F  Cl COSC.sub.3 H.sub.7                                                   7.056                                                                              F  Cl COSCH.sub.2 CHCH.sub.2                                               7.057                                                                              F  Cl COSCH.sub.2 COOCH.sub.3                                              7.058                                                                              F  Cl COSCH.sub.2 COOC.sub.2 H.sub.5                                       7.059                                                                              F  Cl COSCH.sub.2 COOC.sub.5 H.sub.11                                      7.060                                                                              F  Cl                                                                                 ##STR794##                                                          7.061                                                                              F  Cl                                                                                 ##STR795##                                                          7.062                                                                              F  Cl                                                                                 ##STR796##                                                          7.063                                                                              F  Cl COSCH.sub.2 CH.sub.2 COOCH.sub.3                                     7.064                                                                              F  Cl COSCH.sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                           7.065                                                                              F  Cl COOCH.sub.2 COOCH.sub.3                                              7.066                                                                              F  Cl                                                                                 ##STR797##                                                          7.067                                                                              F  Cl COOCH.sub.2 COOC.sub.5 H.sub.11                                      7.068                                                                              F  Cl COOCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                              7.069                                                                              F  Cl COONa                                                                7.070                                                                              F  Cl                                                                                 ##STR798##                                                          7.071                                                                              F  Cl OH                                                                   7.072                                                                              F  Cl OCH.sub.3                                                            7.073                                                                              F  Cl OC.sub.2 H.sub.5                                                     7.074                                                                              F  Cl OC.sub.3 H.sub.7                                                     7.075                                                                              F  Cl                                                                                 ##STR799##                                                          7.076                                                                              F  Cl OC.sub.4 H.sub.9                                                     7.077                                                                              F  Cl                                                                                 ##STR800##                                                          7.078                                                                              F  Cl                                                                                 ##STR801##                                                          7.079                                                                              F  Cl OCH.sub.2 CHCH.sub.2                                                 7.080                                                                              F  Cl                                                                                 ##STR802##                                                          7.081                                                                              F  Cl OCH.sub.2 CHCHCI                                                     7.082                                                                              F  Cl OCH.sub.2 CCH                                                        7.083                                                                              F  Cl                                                                                 ##STR803##                                                          7.084                                                                              F  Cl OCH.sub.2 COOCH.sub.3                                                7.085                                                                              F  Cl OCH.sub.2 COOC.sub.5 H.sub.11                                        7.086                                                                              F  Cl                                                                                 ##STR804##                                                          7.087                                                                              F  Cl OCH.sub.2 COOC.sub.2 H.sub.5                                         7.088                                                                              F  Cl                                                                                 ##STR805##                                                          7.089                                                                              F  Cl OCH.sub.2 CH.sub.2 OCH.sub.3                                         7.090                                                                              F  Cl                                                                                 ##STR806##                                                          7.091                                                                              F  Cl                                                                                 ##STR807##                                                          7.092                                                                              F  Cl                                                                                 ##STR808##                                                          7.093                                                                              F  Cl OCH.sub.2 CH.sub.2 Cl                                                7.094                                                                              F  Cl OCH.sub.2 CN                                                         7.095                                                                              F  Cl                                                                                 ##STR809##                                                          7.096                                                                              F  Cl SCH.sub.3                                                            7.097                                                                              F  Cl SC.sub.2 H.sub.5                                                     7.098                                                                              F  Cl SC.sub.3 H.sub.7                                                     7.099                                                                              F  Cl                                                                                 ##STR810##                                                          7.100                                                                              F  Cl SCH.sub.2CHCH.sub.2                                                  7.101                                                                              F  Cl                                                                                 ##STR811##                                                          7.102                                                                              F  Cl SCH.sub.2 CHCHCI                                                     7.103                                                                              F  Cl SCH.sub.2CCH                                                         7.104                                                                              F  Cl                                                                                 ##STR812##                                                          7.105                                                                              F  Cl SCH.sub.2 COOCH.sub.3                                                7.106                                                                              F  Cl SCH.sub.2 COOC.sub.2 H.sub.5                                         7.107                                                                              F  Cl SCH.sub.2 COOC.sub.5 H.sub.11                                        7.108                                                                              F  Cl                                                                                 ##STR813##                                                          7.109                                                                              F  Cl                                                                                 ##STR814##                                                          7.110                                                                              F  Cl SCH.sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                             7.111                                                                              F  Cl                                                                                 ##STR815##                                                          7.112                                                                              F  Cl                                                                                 ##STR816##                                                          7.113                                                                              F  Cl                                                                                 ##STR817##                                                          7.114                                                                              F  Cl                                                                                 ##STR818##                                                          7.115                                                                              F  Cl                                                                                 ##STR819##                                                          7.116                                                                              F  Cl                                                                                 ##STR820##                                                          7.117                                                                              F  Cl                                                                                 ##STR821##                                                          7.118                                                                              F  Cl                                                                                 ##STR822##                                                          7.119                                                                              F  Cl                                                                                 ##STR823##                                                          7.120                                                                              F  Cl                                                                                 ##STR824##                                                          7.121                                                                              F  Cl                                                                                 ##STR825##                                                          7.122                                                                              F  Cl                                                                                 ##STR826##                                                          7.123                                                                              F  Cl                                                                                 ##STR827##                                                          7.124                                                                              F  Cl                                                                                 ##STR828##                                                          7.125                                                                              F  Cl                                                                                 ##STR829##                                                          7.126                                                                              F  Cl                                                                                 ##STR830##                                                          7.127                                                                              F  Cl                                                                                 ##STR831##                                                          7.128                                                                              F  Cl                                                                                 ##STR832##                                                          7.129                                                                              F  Cl                                                                                 ##STR833##                                                          7.130                                                                              F  Cl                                                                                 ##STR834##                                                          7.131                                                                              F  Cl                                                                                 ##STR835##                                                          7.132                                                                              F  Cl                                                                                 ##STR836##                                                          7.133                                                                              F  CI                                                                                 ##STR837##                                                          7.134                                                                              F  Cl                                                                                 ##STR838##                                                          7.135                                                                              F  Cl                                                                                 ##STR839##                                                          7.136                                                                              F  Cl                                                                                 ##STR840##                                                          7.137                                                                              F  Cl                                                                                 ##STR841##                                                          7.138                                                                              F  Cl                                                                                 ##STR842##                                                          7.139                                                                              F  Cl                                                                                 ##STR843##                                                          7.140                                                                              F  Cl                                                                                 ##STR844##                                                          7.141                                                                              F  Cl                                                                                 ##STR845##                                                          7.142                                                                              F  Cl                                                                                 ##STR846##                                                          7.143                                                                              F  Cl                                                                                 ##STR847##                                                          7.144                                                                              F  Cl                                                                                 ##STR848##                                                          7.145                                                                              F  Cl                                                                                 ##STR849##                                                          7.146                                                                              F  Cl NHSO.sub.2 CH.sub.3                                                  7.147                                                                              F  Cl NHSO.sub.2 C.sub.2 H.sub.5                                           7.148                                                                              F  Cl NHSO.sub.2 Cl                                                        7.149                                                                              F  Cl                                                                                 ##STR850##                                                          7.150                                                                              F  Cl                                                                                 ##STR851##                                                          7.151                                                                              H  Cl COOH                                                                 7.152                                                                              H  Cl COOCH.sub.3                                                          7.153                                                                              H  Cl                                                                                 ##STR852##                                                          7.154                                                                              H  Cl COOC.sub.5 H.sub.11                                                  7.155                                                                              H  Cl COOCH.sub.2 CH.sub.2 OCH.sub.3                                       7.156                                                                              H  Cl COOCH.sub.2 SCH.sub.3                                                7.157                                                                              H  Cl COOH(CH.sub.3)CH.sub.2 SCH.sub.3                                     7.158                                                                              H  Cl                                                                                 ##STR853##                                                          7.159                                                                              H  Cl                                                                                 ##STR854##                                                          7.160                                                                              H  Cl                                                                                 ##STR855##                                                          7.161                                                                              H  Cl                                                                                 ##STR856##                                                          7.162                                                                              H  Cl                                                                                 ##STR857##                                                          7.163                                                                              H  Cl                                                                                 ##STR858##                                                          7.164                                                                              H  Cl                                                                                 ##STR859##                                                          7.165                                                                              H  Cl SC.sub.3 H.sub.7                                                     7.166                                                                              H  Cl COOCH.sub.2 COOCH.sub.3                                              7.167                                                                              H  Cl COOCH(CH.sub.3)COOCH.sub.3                                           7.168                                                                              H  Cl COSCH.sub.2 COOCH.sub.3                                              7.169                                                                              H  Cl COSCH(CH.sub.3)COOCH.sub.3                                           7.170                                                                              H  Cl OH                                                                   7.171                                                                              H  Cl OCH.sub.3                                                            7.172                                                                              H  Cl OC.sub.2 H.sub.5                                                     7.173                                                                              H  Cl                                                                                 ##STR860##                                                          7.174                                                                              H  Cl OCH.sub.2 CCH                                                        7.175                                                                              H  Cl OCH.sub.2 CHCHCl                                                     7.176                                                                              H  Cl                                                                                 ##STR861##                                                          7.177                                                                              H  Cl                                                                                 ##STR862##                                                          7.178                                                                              H  Cl OCH.sub.2 COOCH.sub.3                                                7.179                                                                              H  Cl OCH.sub.2 COOC.sub.2 H.sub.5                                         7.180                                                                              H  Cl OCH(CH.sub.3)COOCH.sub.3                                             7.181                                                                              H  Cl SH                                                                   7.182                                                                              H  Cl SCH.sub.3                                                            7.183                                                                              H  Cl SC.sub.2 H.sub.5                                                     7.184                                                                              H  Cl                                                                                 ##STR863##                                                          7.185                                                                              H  Cl SCH.sub.2 COOCH.sub.3                                                7.186                                                                              H  Cl SCH(CH.sub.3)COOCH.sub.3                                             7.187                                                                              H  Cl SCH.sub.2 COOC.sub.2 H.sub.5                                         7.188                                                                              H  Cl                                                                                 ##STR864##                                                          7.189                                                                              H  Cl                                                                                 ##STR865##                                                          7.190                                                                              H  Cl                                                                                 ##STR866##                                                          7.191                                                                              H  Cl                                                                                 ##STR867##                                                          7.192                                                                              H  Cl                                                                                 ##STR868##                                                          7.193                                                                              H  Cl                                                                                 ##STR869##                                                          7.194                                                                              H  Cl                                                                                 ##STR870##                                                          7.195                                                                              H  Cl                                                                                 ##STR871##                                                          7.196                                                                              H  Cl                                                                                 ##STR872##                                                          7.197                                                                              H  Cl                                                                                 ##STR873##                                                          7.198                                                                              H  Cl                                                                                 ##STR874##                                                          7.199                                                                              H  Cl                                                                                 ##STR875##                                                          7.200                                                                              H  Cl                                                                                 ##STR876##                                                          7.201                                                                              H  Cl                                                                                 ##STR877##                                                          7.202                                                                              H  Cl NHSO.sub.2 C.sub.2 H.sub.5                                           7.203                                                                              H  Cl NHSO.sub.2 CH.sub.2 Cl                                               7.204                                                                              F  CN COOH                                                                 7.205                                                                              F  CN                                                                                 ##STR878##                                                          7.206                                                                              F  CN                                                                                 ##STR879##                                                          7.207                                                                              F  CN OCH.sub.2 CCH                                                        7.208                                                                              F  CN OCH(CH.sub.3)CCH                                                     7.209                                                                              F  CN SCH.sub.2 COOCH.sub.3                                                7.210                                                                              F  CN SCH(CH.sub.3)COOCH.sub.3                                             7.211                                                                              F  CN OCH.sub.2 COOCH.sub.3                                                7.212                                                                              F  CN OCH.sub.2 COOC.sub.5 H.sub.11                                        7.213                                                                              F  CN OCH(CH.sub.3)COOC.sub.2 H.sub.5                                      7.214                                                                              F  CN                                                                                 ##STR880##                                                          7.215                                                                              F  CN                                                                                 ##STR881##                                                          7.216                                                                              F  CN                                                                                 ##STR882##                                                          7.217                                                                              F  CN                                                                                 ##STR883##                                                          7.218                                                                              F  CN                                                                                 ##STR884##                                                          7.219                                                                              F  CN                                                                                 ##STR885##                                                          7.220                                                                              F  CN                                                                                 ##STR886##                                                          7.221                                                                              F  Br COOH                                                                 7.222                                                                              F  Br                                                                                 ##STR887##                                                          7.223                                                                              F  Br OH                                                                   7.224                                                                              F  Br                                                                                 ##STR888##                                                          7.225                                                                              F  Br OCH.sub.2 CCH                                                        7.226                                                                              F  Br OCH(CH.sub.3)CCH                                                     7.227                                                                              F  Br OCH.sub.2 COOCH.sub.3                                                7.228                                                                              F  Br OCH.sub.2 COOC.sub.5 H.sub.11                                        7.229                                                                              F  Br SCH.sub.2 COOCH.sub.3                                                7.230                                                                              F  Br                                                                                 ##STR889##                                                          7.231                                                                              F  Br                                                                                 ##STR890##                                                          7.232                                                                              F  Br                                                                                 ##STR891##                                                          7.233                                                                              F  Cl SCH.sub.2 COOH                                                       __________________________________________________________________________

                  TABLE 8                                                          ______________________________________                                         Compounds of formula Ij                                                         ##STR892##                   (Ij)                                             Comp.                                  phys.                                   No.   R.sub.22                                                                              X.sub.1                                                                               R.sub.19       n.sub.1                                                                            data                                    ______________________________________                                         8.001 F      S      C.sub.3 H.sub.7 (i)                                                                           0   m.p.                                                                           136-137° C.                      8.002 H      S      C.sub.3 H.sub.7 (i)                                                                           0                                           8.003 H      S      CH.sub.2 CCH   0                                           8.004 F      S      CH.sub.2 CCH   0                                           8.005 F      S      CH(CH.sub.3)CCH                                                                               0                                           8.006 H      S      CH(CH.sub.3)CCH                                                                               0                                           8.007 H      S      CH(CH.sub.3)COOCH.sub.3                                                                       0                                           8.008 F      S      CH(CH.sub.3)COOCH.sub.3                                                                       0                                           8.009 H      S      CH.sub.2 COOCH.sub.3                                                                          0                                           8.010 H      S      CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                               0                                           8.011 F      O      C.sub.3 H.sub.7 (i)                                                                           1                                           8.012 H      O      C.sub.3 H.sub.7 (i)                                                                           1                                           8.013 F      O      CH.sub.2 CCH   1                                           8.014 H      O      CH.sub.2 CCH   1                                           8.015 F      O      CH(CH.sub.3)CCH                                                                               1                                           8.016 H      O      CH(CH.sub.3)CCH                                                                               1                                           8.017 H      O      CH.sub.2 COOCH.sub.3                                                                          1                                           8.018 F      O      CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                               1                                           8.019 H      O      CH(CH.sub.3)COOC.sub.3 H.sub.7 (i)                                                            1                                           ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                         Compounds of formula Ik                                                         ##STR893##                   (Ik)                                             Comp.                                                                          No.   R.sub.22                                                                              X.sub.1                                                                               R.sub.19       n.sub.1                                                                            phys. data                              ______________________________________                                         9.001 F      S      C.sub.3 H.sub.7 (i)                                                                           0                                           9.002 H      S      C.sub.3 H.sub.7 (i)                                                                           0                                           9.003 H      S      CH.sub.2CCH    0                                           9.004 F      S      CH.sub.2 CCH   0                                           9.005 F      S      CH(CH.sub.3)C CH                                                                              0                                           9.006 H      S      CH(CH.sub.3)CCH                                                                               0                                           9.007 H      S      CH(CH.sub.3)COOCH.sub.3                                                                       0                                           9.008 F      S      CH(CH.sub.3)COOCH.sub.3                                                                       0                                           9.009 H      S      CH.sub.2 COOCH.sub.3                                                                          0                                           9.010 H      S      CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                               0                                           9.011 F      O      C.sub.3 H.sub.7 (i)                                                                           1                                           9.012 H      O      C.sub.3 H.sub.7 (i)                                                                           1                                           9.013 F      O      CH.sub.2CCH    1                                           9.014 H      O      CH.sub.2CCH    1                                           9.015 F      O      CH(CH.sub.3)CCH                                                                               1                                           9.016 H      O      CH(CH.sub.3)CCH                                                                               1                                           9.017 H      O      CH.sub.2 COOCH.sub.3                                                                          1                                           9.018 F      O      CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                               1                                           9.019 H      O      CH(CH.sub.3)COOC.sub.3 H.sub.7 (i)                                                            1                                           ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                         Compounds of formula Il                                                         ##STR894##                   (Il)                                             Comp.                                                                          No.   R.sub.22                                                                              X.sub.1                                                                              R.sub.19        n.sub.1                                                                            phys. data                              ______________________________________                                         10.001                                                                               F      S     C.sub.3 H.sub.7 (i)                                                                            0                                           10.002                                                                               H      S     C.sub.3 H.sub.7 (i)                                                                            0   m.p.                                                                           > 73° C.                                                                (decomp.)                               10.003                                                                               H      S     CH.sub.2 CCH    0                                           10.004                                                                               F      S     CH.sub.2 CCH    0                                           10.005                                                                               F      S     CH(CH.sub.3)CCH 0                                           10.006                                                                               H      S     CH(CH.sub.3)CCH 0                                           10.007                                                                               H      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           10.008                                                                               F      S     CH(CH.sub.3)COOC.sub.2 H.sub.5                                                                 0   amorphous                               10.009                                                                               H      S     CH.sub.2 COOCH.sub.3                                                                           0                                           10.010                                                                               H      S     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                0                                           10.011                                                                               F      O     C.sub.3 H.sub.7 (i)                                                                            1                                           10.012                                                                               H      O     C.sub.3 H.sub.7 (i)                                                                            1                                           10.013                                                                               F      O     CH.sub.2CCH     1                                           10.014                                                                               H      O     CH.sub.2CCH     1                                           10.015                                                                               F      O     CH(CH.sub.3)CCH 1                                           10.016                                                                               H      O     CH(CH.sub.3)CCH 1                                           10.017                                                                               H      O     CH.sub.2 COOCH.sub.3                                                                           1                                           10.018                                                                               F      O     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                1                                           10.019                                                                               H      O     CH(CH.sub. 3)COOC.sub.3 H.sub.7 (i)                                                            1                                           ______________________________________                                    

                  TABLE 11                                                         ______________________________________                                         Compounds of formula Im                                                         ##STR895##                   (Im)                                             Comp.                                                                          No.   R.sub.22                                                                              X.sub.1                                                                              R.sub.19        n.sub.1                                                                            phys. data                              ______________________________________                                         11.001                                                                               F      S     C.sub.3 H.sub.7 (i)                                                                            0                                           11.002                                                                               H      S     C.sub.3 H.sub.7 (i)                                                                            0                                           11.003                                                                               H      S     CH.sub.2CCH     0                                           11.004                                                                               F      S     CH.sub.2CCH     0                                           11.005                                                                               F      S     CH(CH.sub.3)CCH 0                                           11.006                                                                               H      S     CH(CH.sub.3)CCH 0                                           11.007                                                                               H      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           11.008                                                                               F      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           11.009                                                                               H      S     CH.sub.2 COOCH.sub.3                                                                           0                                           11.010                                                                               H      S     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                0                                           11.011                                                                               F      O     C.sub.3 H.sub.7 (i)                                                                            1                                           11.012                                                                               H      O     C.sub.3 H.sub.7 (i)                                                                            1                                           11.013                                                                               F      O     CH.sub.2 CCH    1                                           11.014                                                                               H      O     CH.sub.2 CCH    1                                           11.015                                                                               F      O     CH(CH.sub.3)CCH 1                                           11.016                                                                               H      O     CH(CH.sub.3)CCH 1                                           11.017                                                                               H      O     CH.sub.2 COOCH.sub.3                                                                           1                                           11.018                                                                               F      O     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                1                                           11.019                                                                               H      O     CH(CH.sub.3)COOC.sub.3 H.sub.7 (i)                                                             1                                           ______________________________________                                    

                  TABLE 12                                                         ______________________________________                                         Compounds of formula In                                                         ##STR896##                   (In)                                             Comp.                                                                          No.   R.sub.22                                                                              X.sub.1                                                                              R.sub.19        n.sub.1                                                                            phys. data                              ______________________________________                                         12.001                                                                               F      S     C.sub.3 H.sub.7 (i)                                                                            0                                           12.002                                                                               H      S     C.sub.3 H.sub.7 (i)                                                                            0                                           12.003                                                                               H      S     CH.sub.2 CCH    0                                           12.004                                                                               F      S     CH.sub.2 CCH    0                                           12.005                                                                               F      S     CH(CH.sub.3)C CH                                                                               0                                           12.006                                                                               H      S     CH(CH.sub.3)CCH 0                                           12.007                                                                               H      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           12.008                                                                               F      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           12.009                                                                               H      S     CH.sub.2 COOCH.sub.3                                                                           0                                           12.010                                                                               H      S     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                0                                           12.011                                                                               F      O     C.sub.3 H.sub.7 (i)                                                                            1                                           12.012                                                                               H      O     C.sub.3 H.sub.7 (i)                                                                            1                                           12.013                                                                               F      O     CH.sub.2 CCH    1                                           12.014                                                                               H      O     CH.sub.2 CCH    1                                           12.015                                                                               F      O     CH(CH.sub.3)CCH 1                                           12.016                                                                               H      O     CH(CH.sub.3)CCH 1                                           12.017                                                                               H      O     CH.sub.2 COOCH.sub.3                                                                           1                                           12.018                                                                               F      O     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                1                                           12.019                                                                               H      O     CH(CH.sub.3)COOC.sub.3 H.sub.7 (i)                                                             1                                           ______________________________________                                    

                  TABLE 13                                                         ______________________________________                                         Compounds of formula Io                                                         ##STR897##                   (Io)                                             Comp.                                                                          No.   R.sub.22                                                                              X.sub.1                                                                              R.sub.19        n.sub.1                                                                            phys. data                              ______________________________________                                         13.001                                                                               F      S     C.sub.3 H.sub.7 (i)                                                                            0                                           13.002                                                                               H      S     C.sub.3 H.sub.7 (i)                                                                            0                                           13.003                                                                               H      S     CH.sub.2 CCH    0                                           13.004                                                                               F      S     CH.sub.2 CCH    0                                           13.005                                                                               F      S     CH(CH.sub.3)C CH                                                                               0                                           13.006                                                                               H      S     CH(CH.sub.3)CCH 0                                           13.007                                                                               H      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           13.008                                                                               F      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           13.009                                                                               H      S     CH.sub.2 COOCH.sub.3                                                                           0                                           13.010                                                                               H      S     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                0                                           13.011                                                                               F      O     C.sub.3 H.sub.7 (i)                                                                            1                                           13.012                                                                               H      O     C.sub.3 H.sub.7 (i)                                                                            1                                           13.013                                                                               F      O     CH.sub.2CCH     1                                           13.014                                                                               H      O     CH.sub.2CCH     1                                           13.015                                                                               F      O     CH(CH.sub.3)CCH 1                                           13.016                                                                               H      O     CH(CH.sub.3)CCH 1                                           13.017                                                                               H      O     CH.sub.2 COOCH.sub.3                                                                           1                                           13.018                                                                               F      O     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                1                                           13.019                                                                               H      O     CH(CH.sub.3)COOC.sub.3 H.sub.7 (i)                                                             1                                           ______________________________________                                    

                  TABLE 14                                                         ______________________________________                                         Compounds of formula Ip                                                         ##STR898##                   (Ip)                                             Comp.                                                                          No.   R.sub.22                                                                              X.sub.1                                                                              R.sub.19        n.sub.1                                                                            phys. data                              ______________________________________                                         14.001                                                                               F      S     C.sub.3 H.sub.7 (i)                                                                            0                                           14.002                                                                               H      S     C.sub.3 H.sub.7 (i)                                                                            0                                           14.003                                                                               H      S     CH.sub.2 CCH    0                                           14.004                                                                               F      S     CH.sub.2 CCH    0                                           14.005                                                                               F      S     CH(CH.sub.3)C CH                                                                               0                                           14.006                                                                               H      S     CH(CH.sub.3)CCH 0                                           14.007                                                                               H      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           14.008                                                                               F      S     CH(CH.sub.3)COOCH.sub.3                                                                        0                                           14.009                                                                               H      S     CH.sub.2 COOCH.sub.3                                                                           0                                           14.010                                                                               H      S     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                0                                           14.011                                                                               F      O     C.sub.3 H.sub.7 (i)                                                                            1                                           14.012                                                                               H      O     C.sub.3 H.sub.7 (i)                                                                            1                                           14.013                                                                               F      O     CH.sub.2 CCH    1                                           14.014                                                                               H      O     CH.sub.2 CCH    1                                           14.015                                                                               F      O     CH(CH.sub.3)CCH 1                                           14.016                                                                               H      O     CH(CH.sub.3)CCH 1                                           14.017                                                                               H      O     CH.sub.2 COOCH.sub.3                                                                           1                                           14.018                                                                               F      O     CH.sub.2 COOC.sub.3 H.sub.7 (i)                                                                1                                           14.019                                                                               H      O     CH(CH.sub.3)COOC.sub.3 H.sub.7 (i)                                                             1                                           ______________________________________                                    

                                      TABLE 15                                     __________________________________________________________________________     Compounds of formula Iq                                                         ##STR899##                           (Iq)                                     Comp. No.                                                                            R.sub.1                                                                           R.sub.2                                                                           A                      phys. data                                  __________________________________________________________________________     15.001                                                                               F  Cl H                                                                  15.002                                                                               F  Cl CN                                                                 15.003                                                                               F  Cl NO.sub.2                                                           15.004                                                                               F  Cl COOH                                                               15.005                                                                               F  Cl COOCH.sub.3            resin                                       15.006                                                                               F  Cl COOC.sub.2 H.sub.5                                                 15.007                                                                               F  Cl COOC.sub.3 H.sub.7                                                 15.008                                                                               F  Cl COOCH(CH.sub.3).sub.2                                              15.009                                                                               F  Cl COOC.sub.4 H.sub.9                                                 15.010                                                                               F  Cl                                                                                 ##STR900##                                                        15.011                                                                               F  Cl                                                                                 ##STR901##                                                        15.012                                                                               F  Cl COOC.sub.5 H.sub.11                                                15.013                                                                               F  Cl  COOCH.sub.2 CH.sub.2 OCH.sub.3                                    15.014                                                                               F  Cl COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                              15.015                                                                               F  Cl COOCH(CH.sub.3)CH.sub.2 OCH.sub.3                                  15.016                                                                               F  Cl COOCH.sub.2 CH.sub.2 SCH.sub.3                                     15.017                                                                               F  Cl COOCH(CH.sub.3)CH.sub.2 SCH.sub.3                                  15.018                                                                               F  Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.2 H.sub.5                           15.019                                                                               F  Cl COOCH(CH.sub.3)CH.sub.2SC.sub.3 H.sub.7                            15.020                                                                               F  Cl                                                                                 ##STR902##                                                        15.021                                                                               F  Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.4 H.sub.9                           15.022                                                                               F  Cl COOCH(CH.sub.3)CH.sub.2 SC.sub.5 H.sub.11                          15.023                                                                               F  Cl                                                                                 ##STR903##                                                        15.024                                                                               F  Cl                                                                                 ##STR904##                                                        15.025                                                                               F  Cl CONH.sub.2                                                         15.026                                                                               F  Cl CONHCH.sub.3                                                       15.027                                                                               F  Cl                                                                                 ##STR905##                                                        15.028                                                                               F  Cl                                                                                 ##STR906##                                                        15.029                                                                               F  Cl                                                                                 ##STR907##                                                        15.030                                                                               F  Cl CONHCH.sub.2 CHCH.sub.2                                            15.031                                                                               F  Cl CON(CH.sub.2 CHCH.sub.2).sub.2                                     15.032                                                                               F  Cl                                                                                 ##STR908##                                                        15.033                                                                               F  Cl                                                                                 ##STR909##                                                        15.034                                                                               F  Cl                                                                                 ##STR910##                                                        15.035                                                                               F  Cl                                                                                 ##STR911##                                                        15.036                                                                               F  Cl                                                                                 ##STR912##                                                        15.037                                                                               F  Cl                                                                                 ##STR913##                                                        15.038                                                                               F  Cl COOCH.sub.2CH.sub.2Cl                                              15.039                                                                               F  Cl COOCH.sub.2 CN                                                     15.040                                                                               F  Cl                                                                                 ##STR914##                                                        15.041                                                                               F  Cl COOCH.sub.2CHCH.sub.2                                              15.042                                                                               F  Cl COOCH.sub.2 CHCHCl                                                 15.043                                                                               F  Cl                                                                                 ##STR915##                                                        15.044                                                                               F  Cl COOCH.sub.2 CCH                                                    15.045                                                                               F  Cl                                                                                 ##STR916##                                                        15.046                                                                               F  Cl                                                                                 ##STR917##                                                        15.047                                                                               F  Cl                                                                                 ##STR918##                                                        15.048                                                                               F  Cl                                                                                 ##STR919##                                                        15.049                                                                               F  Cl                                                                                 ##STR920##                                                        15.050                                                                               F  Cl                                                                                 ##STR921##                                                        15.051                                                                               F  Cl                                                                                 ##STR922##                                                        15.052                                                                               F  Cl                                                                                 ##STR923##                                                        15.053                                                                               F  Cl COSCH.sub.3                                                        15.054                                                                               F  Cl COSC.sub.2 H.sub.5                                                 15.055                                                                               F  Cl COSC.sub.3 H.sub.7                                                 15.056                                                                               F  Cl COSCH.sub.2 CH CH.sub.2                                            15.057                                                                               F  Cl COSCH.sub.2 COOCH.sub.3                                            15.058                                                                               F  Cl COSCH.sub.2 COOC.sub.2 H.sub.5                                     15.059                                                                               F  Cl COSCH.sub.2 COOC.sub.5 H.sub.11                                    15.060                                                                               F  Cl                                                                                 ##STR924##                                                        15.061                                                                               F  Cl                                                                                 ##STR925##                                                        15.062                                                                               F  Cl                                                                                 ##STR926##                                                        15.063                                                                               F  Cl COSCH.sub.2 CH.sub.2 COOCH.sub.3                                   15.064                                                                               F  Cl COSCH.sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                         15.065                                                                               F  Cl COOCH.sub.2 COOCH.sub.3                                            15.066                                                                               F  Cl                                                                                 ##STR927##                                                        15.067                                                                               F  Cl COOCH.sub.2 COOC.sub.5 H.sub.11                                    15.068                                                                               F  Cl COOCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                            15.069                                                                               F  Cl COONa                                                              15.070                                                                               F  Cl                                                                                 ##STR928##                                                        15.071                                                                               F  Cl OH                                                                 15.072                                                                               F  Cl  OCH.sub.3                                                         15.073                                                                               F  Cl OC.sub.2 H.sub.5                                                   15.074                                                                               F  Cl OC.sub.3 H.sub.7                                                   15.075                                                                               F  Cl                                                                                 ##STR929##            resin                                       15.076                                                                               F  Cl OC.sub.4 H.sub.9                                                   15.077                                                                               F  Cl                                                                                 ##STR930##                                                        15.078                                                                               F  Cl                                                                                 ##STR931##                                                        15.079                                                                               F  Cl OCH.sub.2 CHCH.sub.2                                               15.080                                                                               F  Cl                                                                                 ##STR932##                                                        15.081                                                                               F  Cl OCH.sub.2 CHCHCl                                                   15.082                                                                               F  Cl OCH.sub.2 CCH                                                      15.083                                                                               F  Cl                                                                                 ##STR933##                                                        15.084                                                                               F  Cl OCH.sub.2 COOCH.sub.3                                              15.085                                                                               F  Cl OCH.sub.2 COOC.sub.5 H.sub.11                                      15.086                                                                               F  Cl                                                                                 ##STR934##                                                        15.087                                                                               F  Cl OCH.sub.2 COOC.sub.2 H.sub.5                                       15.088                                                                               F  Cl                                                                                 ##STR935##                                                        15.089                                                                               F  Cl OCH.sub.2 CH.sub.2 OCH.sub.3                                       15.090                                                                               F  Cl                                                                                 ##STR936##                                                        15.091                                                                               F  Cl                                                                                 ##STR937##                                                        15.092                                                                               F  Cl                                                                                 ##STR938##                                                        15.093                                                                               F  Cl OCH.sub.2 CH.sub.2 Cl                                              15.094                                                                               F  Cl OCH.sub.2 CN                                                       15.095                                                                               F  Cl                                                                                 ##STR939##                                                        15.096                                                                               F  Cl SCH.sub.3                                                          15.097                                                                               F  Cl SC.sub.2 H.sub.5                                                   15.098                                                                               F  Cl SC.sub.3 H.sub.7                                                   15.099                                                                               F  Cl                                                                                 ##STR940##                                                        15.100                                                                               F  Cl SCH.sub.2 CHCH.sub.2                                               15.101                                                                               P  Cl                                                                                 ##STR941##                                                        15.102                                                                               F  Cl S CH.sub.2 CHCHCl                                                  15.103                                                                               F  Cl SCH.sub.2 CCH                                                      15.104                                                                               F  Cl                                                                                 ##STR942##                                                        15.105                                                                               F  Cl SCH.sub.2 COOCH.sub.3  resin                                       15.106                                                                               F  Cl SCH.sub.2 COOC.sub.2 H.sub.5                                       15.107                                                                               F  Cl SCH.sub.2 COOC.sub.5 H.sub.11                                      15.108                                                                               F  Cl                                                                                 ##STR943##                                                        15.109                                                                               F  Cl                                                                                 ##STR944##                                                        15.110                                                                               F  Cl SCH.sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                           15.111                                                                               F  Cl                                                                                 ##STR945##                                                        15.112                                                                               F  Cl                                                                                 ##STR946##                                                        15.113                                                                               F  Cl                                                                                 ##STR947##                                                        15.114                                                                               F  Cl                                                                                 ##STR948##                                                        15.115                                                                               F  Cl                                                                                 ##STR949##                                                        15.116                                                                               F  Cl                                                                                 ##STR950##                                                        15.117                                                                               F  Cl                                                                                 ##STR951##                                                        15.118                                                                               F  Cl                                                                                 ##STR952##                                                        15.119                                                                               F  Cl                                                                                 ##STR953##                                                        15.120                                                                               F  Cl                                                                                 ##STR954##                                                        15.121                                                                               F  Cl                                                                                 ##STR955##                                                        15.122                                                                               F  Cl                                                                                 ##STR956##                                                        15.123                                                                               F  Cl                                                                                 ##STR957##                                                        15.124                                                                               F  Cl                                                                                 ##STR958##                                                        15.125                                                                               F  Cl                                                                                 ##STR959##                                                        15.126                                                                               F  Cl                                                                                 ##STR960##                                                        15.127                                                                               F  Cl                                                                                 ##STR961##                                                        15.128                                                                               F  Cl                                                                                 ##STR962##                                                        15.129                                                                               F  Cl                                                                                 ##STR963##                                                        15.130                                                                               F  Cl                                                                                 ##STR964##                                                        15.131                                                                               F  Cl                                                                                 ##STR965##                                                        15.132                                                                               F  Cl                                                                                 ##STR966##                                                        15.133                                                                               F  Cl                                                                                 ##STR967##                                                        15.134                                                                               F  Cl                                                                                 ##STR968##                                                        15.135                                                                               F  Cl                                                                                 ##STR969##                                                        15.136                                                                               F  Cl                                                                                 ##STR970##                                                        15.137                                                                               F  Cl                                                                                 ##STR971##                                                        15.138                                                                               F  Cl                                                                                 ##STR972##                                                        15.139                                                                               F  Cl                                                                                 ##STR973##                                                        15.140                                                                               F  Cl                                                                                 ##STR974##                                                        15.141                                                                               F  Cl                                                                                 ##STR975##                                                        15.142                                                                               F  Cl                                                                                 ##STR976##                                                        15.143                                                                               F  Cl                                                                                 ##STR977##                                                        15.144                                                                               F  Cl                                                                                 ##STR978##                                                        15.145                                                                               F  Cl                                                                                 ##STR979##                                                        15.146                                                                               F  Cl NHSO.sub.2 CH.sub.3                                                15.147                                                                               F  Cl NHSO.sub.2 C.sub.2 H.sub.5                                         15.148                                                                               F  Cl NHSO.sub.2 Cl                                                      15.149                                                                               F  Cl                                                                                 ##STR980##                                                        15.150                                                                               F  Cl                                                                                 ##STR981##                                                        15.151                                                                               H  Cl COOH                                                               15.152                                                                               H  Cl COOCH.sub.3            m.p.                                                                           138-141° C.                          15.153                                                                               H  Cl                                                                                 ##STR982##                                                        15.154                                                                               H  Cl COOC.sub.5 H.sub.11                                                15.155                                                                               H  Cl COOCH.sub.2 CH.sub.2 OCH.sub.3                                     15.156                                                                               H  Cl COOCH.sub.2 SCH.sub.3                                              15.157                                                                               H  Cl COOCH(CH.sub.3)CH.sub.2 SCH.sub.3                                  15.158                                                                               H  Cl                                                                                 ##STR983##                                                        15.159                                                                               H  Cl                                                                                 ##STR984##                                                        15.160                                                                               H  Cl                                                                                 ##STR985##                                                        15.161                                                                               H  Cl                                                                                 ##STR986##                                                        15.162                                                                               H  Cl                                                                                 ##STR987##                                                        15.163                                                                               H  Cl                                                                                 ##STR988##                                                        15.164                                                                               H  Cl                                                                                 ##STR989##                                                        15.165                                                                               H  Cl SC.sub.3 H.sub.7                                                   15.166                                                                               H  Cl COOCH.sub.2 COOCH.sub.3                                            15.167                                                                               H  Cl COOCH(CH.sub.3)COOCH.sub.3                                         15.168                                                                               H  Cl COSCH.sub.2 COOCH.sub.3                                            15.169                                                                               H  Cl COSCH(CH.sub.3)COOCH.sub.3                                         15.170                                                                               H  Cl OH                                                                 15.171                                                                               H  Cl OCH.sub.3                                                          15.172                                                                               H  Cl OC.sub.2 H.sub.5                                                   15.173                                                                               H  Cl                                                                                 ##STR990##                                                        15.174                                                                               H  Cl OCH.sub.2 C CH                                                     15.175                                                                               H  Cl OCH.sub.2 CHCHCl                                                   15.176                                                                               H  Cl                                                                                 ##STR991##                                                        15.177                                                                               H  Cl                                                                                 ##STR992##                                                        15.178                                                                               H  Cl OCH.sub.2 COOCH.sub.3                                              15.179                                                                               H  Cl OCH.sub.2 COOC.sub.2 H.sub.5                                       15.180                                                                               H  Cl OCH(CH.sub.3)COOCH.sub.3                                           15.181                                                                               H  Cl SH                                                                 15.182                                                                               H  Cl SCH.sub.3                                                          15.183                                                                               H  Cl SC.sub.2 H.sub.5                                                   15.184                                                                               H  Cl                                                                                 ##STR993##                                                        15.185                                                                               H  Cl SCH.sub.2 COOCH.sub.3                                              15.186                                                                               H  Cl SCH(CH.sub.3)COOCH.sub.3                                           15.187                                                                               H  Cl SCH.sub.2 COOC.sub.2 H.sub.5                                       15.188                                                                               H  Cl                                                                                 ##STR994##                                                        15.189                                                                               H  Cl                                                                                 ##STR995##                                                        15.190                                                                               H  Cl                                                                                 ##STR996##                                                        15.191                                                                               H  Cl                                                                                 ##STR997##                                                        15.192                                                                               H  Cl                                                                                 ##STR998##                                                        15.193                                                                               H  Cl                                                                                 ##STR999##                                                        15.194                                                                               H  Cl                                                                                 ##STR1000##                                                       15.195                                                                               H  Cl                                                                                 ##STR1001##                                                       15.196                                                                               H  Cl                                                                                 ##STR1002##                                                       15.197                                                                               H  Cl                                                                                 ##STR1003##                                                       15.198                                                                               H  Cl                                                                                 ##STR1004##                                                       15.199                                                                               H  Cl                                                                                 ##STR1005##                                                       15.200                                                                               H  Cl                                                                                 ##STR1006##                                                       15.201                                                                               H  Cl                                                                                 ##STR1007##                                                       15.202                                                                               H  Cl NHSO.sub.2 C.sub.2 H.sub.5                                         15.203                                                                               H  Cl NHSO.sub.2 CH.sub.2 Cl                                             15.204                                                                               F  CN COOH                                                               15.205                                                                               F  CN                                                                                 ##STR1008##                                                       15.206                                                                               F  CN                                                                                 ##STR1009##                                                       15.207                                                                               F  CN OCH.sub.2 CCH                                                      15.208                                                                               F  CN OCH(CH.sub.3)CCH                                                   15.209                                                                               F  CN SCH.sub.2 COOCH.sub.3                                              15.210                                                                               F  CN SCH(CH.sub.3)COOCH.sub.3                                           15.211                                                                               F  CN OCH.sub.2 COOCH.sub.3                                              15.212                                                                               F  CN OCH.sub.2 COOC.sub.5 H.sub.11                                      15.213                                                                               F  CN OCH(CH.sub.3)COOC.sub.2 H.sub.5                                    15.214                                                                               F  CN                                                                                 ##STR1010##                                                       15.215                                                                               F  CN                                                                                 ##STR1011##                                                       15.216                                                                               F  CN                                                                                 ##STR1012##                                                       15.217                                                                               F  CN                                                                                 ##STR1013##                                                       15.218                                                                               F  CN                                                                                 ##STR1014##                                                       15.219                                                                               F  CN                                                                                 ##STR1015##                                                       15.220                                                                               F  CN                                                                                 ##STR1016##                                                       15.221                                                                               F  Br COOH                                                               15.222                                                                               F  Br                                                                                 ##STR1017##                                                       15.223                                                                               F  Br OH                                                                 15.224                                                                               F  Br                                                                                 ##STR1018##                                                       15.225                                                                               F  Br OCH.sub.2 CCH                                                      15.226                                                                               F  Br OCH(CH.sub.3 )CCH                                                  15.227                                                                               F  Br OCH.sub.2 COOCH.sub.3                                              15.228                                                                               F  Br OCH.sub.2 COOC.sub.5 H.sub.11                                      15.229                                                                               F  Br SCH.sub.2 COOCH.sub.3                                              15.230                                                                               F  Br                                                                                 ##STR1019##                                                       15.231                                                                               F  Br                                                                                 ##STR1020##                                                       15.232                                                                               F  Br                                                                                 ##STR1021##                                                       15.233                                                                               F  Cl SCH.sub.2 COOH                                                     __________________________________________________________________________

B. Formulation Examples for liquid active ingredients of formula I (throughout, percentages are by weight)

    ______________________________________                                         1. Emulsifiable concentrates                                                                         a)     b)       c)                                       ______________________________________                                         a compound of Tables 1-15                                                                            25%    40%      50%                                      calcium dodecylbenzenesulfonate                                                                       5%     8%       6%                                      castor oil polyethylene glycol                                                 ether (36 mol of ethylene oxide)                                                                      5%    --       --                                       tributylphenol polyethylene glycol                                             ether (30 mol of ethylene oxide)                                                                     --     12%       4%                                      cyclohexanone         --     15%      20%                                      xylene mixture        65%    25%      20%                                      ______________________________________                                    

Emulsions of any desired concentration can be produced from such concentrates by dilution with water.

    ______________________________________                                         2. Solutions     a)      b)      c)    d)                                      ______________________________________                                         a compound of Tables 1-15                                                                       80%     10%      5%   95%                                     propylene glycol monomethyl                                                                     20%     --      --    --                                      ether                                                                          polyethylene glycol                                                                             --      70%     --                                            (mol. wt. 400)                                                                 N-methyl-2-pyrrolidone                                                                          --      20%     --    --                                      epoxidised coconut oil                                                                          --      --       1%    5%                                     petroleum fraction (boiling                                                    range 160-190° C.)                                                                       --      --      94%   --                                      ______________________________________                                    

These solutions are suitable for application in the form of micro-drops.

    ______________________________________                                         3. Granules      a)       b)     c)     d)                                     ______________________________________                                         a compound of Tables 1-15                                                                        5%      10%     8%    21%                                    kaolin           94%      --     79%    54%                                    highly dispersed silicic acid                                                                    1%      --     13%     7%                                    attapulgite      --       90%    --     18%                                    ______________________________________                                    

The active ingredient is dissolved in methylene chloride, the solution is sprayed onto the carrier, and the solvent is subsequently evaporated off in vacuo.

    ______________________________________                                         4. Dusts            a)      b)                                                 ______________________________________                                         a compound of Tables 1-15                                                                          2%      5%                                                 highly dispersed silicic acid                                                                      1%      5%                                                 talcum              97%     --                                                 kaolin              --      90%                                                ______________________________________                                    

Ready-for-use dusts are obtained by intimately mixing the carriers with the active ingredient.

Formulation Examples for solid active ingredients of formula I (throughout, percentages are by weight)

    ______________________________________                                         5. Wettable powders a)       b)     c)                                         ______________________________________                                         a compound of Tables 1-15                                                                          25%      50%    75%                                        sodium lignosulfonate                                                                               5%       5%    --                                         sodium laurylsulfate                                                                                3%      --      5%                                        sodium diisobutylnaphthalene-                                                                      --        6%    10%                                        sulfonate                                                                      octylphenol polyethylene glycol                                                                    --        2%    --                                         ether (7-8 mol of ethylene oxide)                                              highly dispersed silicic acid                                                                       5%      10%    10%                                        kaolin              62%      27%    --                                         ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of the desired concentration.

    ______________________________________                                         6. Emulsifiable concentrate                                                    ______________________________________                                         a compound of Tables 1-15                                                                            10%                                                      octylphenol polyethylene glycol                                                                      3%                                                       ether (4-5 mol of ethylene oxide)                                              calcium dodecylbenzenesulfonate                                                                      3%                                                       castor oil polyglycol ether                                                                          4%                                                       (36 mol of ethylene oxide)                                                     cyclohexanone         30%                                                      xylene mixture        50%                                                      ______________________________________                                    

Emulsions of any required concentration can be obtained from this concentrate by dilution with water.

    ______________________________________                                         7. Dusts             a)     b)                                                 ______________________________________                                         a compound of Tables 1-15                                                                            5%     8%                                                talcum               95%    --                                                 kaolin               --     92%                                                ______________________________________                                    

Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill.

    ______________________________________                                         8. Extruder granules                                                           ______________________________________                                         a compound of Tables 1-15                                                                          10%                                                        sodium lignosulfonate                                                                               2%                                                        carboxymethylcellulose                                                                              1%                                                        kaolin              87%                                                        ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

    ______________________________________                                         9. Coated granules                                                             ______________________________________                                         a compound of Tables 1-15                                                                             3%                                                      polyethylene glycol (mol. wt. 200)                                                                    3%                                                      kaolin                 94%                                                     ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

    ______________________________________                                         10. Suspension concentrate                                                     ______________________________________                                         a compound of Tables 1-15                                                                            40%                                                      propylene glycol      10%                                                      nonylphenol polyethylene glycol                                                                       6%                                                      ether (15 mol of ethylene oxide)                                               sodium lignosulfonate 10%                                                      carboxymethylcellulose                                                                                1%                                                      silicone oil in the form of a 75%                                                                     1%                                                      aqueous emulsion                                                               water                 32%                                                      ______________________________________                                    

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

C. Biological Examples: Example B 1 Description of test for preemergence herbicidal action

The seeds of monocotyledonous and dicotyledonous test plants are sown in plastic pots containing standard soil. Immediately after sowing, an aqueous suspension of the test compounds, prepared from a 25% wettable powder formulation (Formulation Example 5), corresponding to a concentration of 2 kg of a.i./ha (500 l water/ha) is applied. The test plants are then cultivated in a greenhouse under optimum conditions. After 3 weeks the test is evaluated in accordance with a scale of nine ratings (1=total damage, 9=no action). Ratings of 1 to 4 (especially 1 to 3) indicate good to very good herbicidal action. The same results are obtained with solutions (Formulation Example 2), dispersible granules (Formulation Example 3), an emulsifiable concentrate (Formulation Examples 1 and 6) and a suspension concentrate (Formulation Example 10), dusts (Formulation Examples 4 and 7) and extruder granules and coated granules (Formulation Examples 8 and 9).

Test plants: Avena, Setaria, Sinapis, Stellaria

The compounds of Tables 1-15 exhibit pronounced herbicidal action in this test. Examples of the good herbicidal action are listed in Table B 1.

                  TABLE B1                                                         ______________________________________                                         Preemergence action                                                                    Conc.                                                                  Comp. No.                                                                              [kg a.i/ha]                                                                              Avena    Setaria                                                                              Sinapis                                                                               Stellaria                              ______________________________________                                         1.075   2         3        1     1      1                                      3.005   2         1        1     1      1                                      3.075   2         2        1     1      1                                      6.075   2         4        1     1      5                                      8.001   2         4        1     1      1                                      ______________________________________                                    

Example B2 Description of test for postemergence herbicidal action (contact herbicide)

Monocotyledonous and dicotyledonous test plants are raised in a greenhouse in plastic pots containing standard soil and in the 4- to 6-leaf stage are sprayed with an aqueous suspension of the test compounds, prepared from a 25% wettable powder formulation (Formulation Example 5), corresponding to a concentration of 2 kg of a.i./ha (500 1 water/ha). The test plants are then grown on in the greenhouse under optimum conditions. After about 18 days the test is evaluated in accordance with a scale of nine ratings (1=total damage, 9=no action). Ratings of 1 to 4 (especially 1 to 3) indicate good to very good herbicidal action. The same results are obtained with solutions (Formulation Example 2), dispersible granules (Formulation Example 3), an emulsifiable concentrate (Formulation Examples 1 and 6) and a suspension concentrate (Formulation Example 10), dusts (Formulation Examples 4 and 7) and extruder granules and coated granules (Formulation Examples 8 and 9).

Test plants: Avena, Setaria, Sinapis, Stellaria

In this test also, the compounds of formula I according to the examples given in Tables 1 to 15 exhibit good herbicidal action.

Examples of the good herbicidal action of compounds of formula I are given in Table B2.

                  TABLE B2                                                         ______________________________________                                         Postemergence action                                                                   Conc.                                                                  Comp. No.                                                                              [kg a.i/ha]                                                                              Avena    Setaria                                                                              Sinapis                                                                               Stellaria                              ______________________________________                                         1.075   2         4        2     1      2                                      3.005   2         2        1     1      1                                      3.075   2         2        1     1      1                                      3.105   2         6        2     1      2                                      8.001   2         2        2     1      1                                      ______________________________________                                     

What is claimed is:
 1. A thiadiazabicyclooctane of formula I ##STR1022## wherein Z is oxygen or sulfur;R₅₃ is C₁ -C₆ alkyl, R₅₄ is C₁ -C₆ alkoxy, C₃ -C₆ alkenyloxy, C₃ -C₆ alkynyloxy, hydroxy or C₁ -C₆ haloalkoxy; or R₅₃ and R₅₄, together with the carbon atom to which they are bonded, form an unsubstituted 3-, 4-, 5- or 6-membered saturated carbocylic ring; W is a group of formulae W₁ to W₁₀ ##STR1023## wherein R₁, R₂₂, R₂₃, R₂₄, R₂₇, R₃₀, R₃₃, R₃₈ and R₄₁ are each independently of the others hydrogen or halogen; R₂ is hydrogen, cyano, nitro, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkoxy or C₁ -C₄ haloalkyl; A is hydrogen, cyano, nitro, ##STR1024## A₁ is cyano or --COR₁₆ ; R₃ is halogen, --X₄ --R₅, amino, C₁ -C₄ alkylamino, di-C₁ -C₄ alkylamino, C₂ -C₄ haloalkylamino, di-C₂ -C₄ haloalkylamino, C₁ -C₄ -dalkoxyalkylamino, di-C₁ --C₄ alkoxyalkyl-amino, C₃ - or C₄ -alkenylamino, diallylamino,-N-pyrrolidino, -N-piperidino, -N-morpholino, -N-thiomorpholino, -N-piperazino, --O--N═C(CH₃)--CH₃ or --O--CH₂ --CH₂ --O--N═C(CH₃)--CH₃ ; R₄, R₄₂ and R₄₃ are each independently of the others hydrogen, C₁ -C₁₀ alkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, C₁ -C₈ haloalkyl, C₂ -C₈ alkenyl, C₂ -C₈ haloalkenyl, C₃ -C₈ alkynyl, C₃ -C₇ cycloalkyl, halo-C₃ -C₇ cycloalkyl, C₁ -C₈ alkylcarbonyl, allylcarbonyl, C₃ -C₇ cycloalkylcarbonyl, benzoyl that is unsubstituted or is substituted at the phenyl ring by one to three identical or different substituents selected from halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy and C₁ -C₄ alkoxy; C₁ -C₆ alkyl substituted by cyano, nitro, carboxy, C₁ -C₈ alkylthio-C₁ -C₈ alkoxycarbonyl, phenyl, halophenyl, C₁ -C₄ alkylphenyl, C₁ -C₄ alkoxyphenyl, C₁ -C₄ haloalkylphenyl, C₁ -C₄ haloalkoxyphenyl, C₁ -C₆ alkoxycarbonyl, C₁ -C₄ alkoxy-C₁ -C₈ alkoxycarbonyl, C₃ -C₈ lkenyloxycarbonyl, C₃ -C₈ alkynyloxycarbonyl, C.sub. 1 -C₈ alkylthiocarbonyl, C₃ -C₈ alkenylthiocarbonyl, C₃ -C₈ alkynylthiocarbonyl, carbamoyl, C₁ -C₄ alkylaminocarbonyl, di-C₁ -C₄ alkylaminocarbonyl; phenylaminocarbonyl that is unsubstituted or is substituted at the phenyl by one to three identical or different substituents selected from halogen, C₁ -C₄ alkyl, C₁ -C₄ haloakkyl, C₁ -C₄ haloalkoxy and C₁ -C₄ alkoxy or by one substituent selected from cyano and nitro; dioxolan-2-yl that is unsubstituted or substituted by one or two C₁ -C₄ alkyl radicals; or dioxanyl that is unsubstituted or substituted by one or two C₁ -C₄ alkyl radicals; R₅ is hydrogen, C₁ -C₁₀ alkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₂ -C₈ haloalkyl, C₁ -C₁₀ alkyl-thio-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, cyano-C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ haloalkenyl, C₃ -C₈ alkynyl, C₃ -C₇ cycloalkyl, C₃ -C₇ cycloalkyl-C₁ -C₄ alkyl, halo-C₃ -C₇ cycloalkyl, or benzyl that is unsubstituted or is substituted at the phenyl ting by one to three identical or different substituents selected from halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy and C₁ -C₄ alkoxy; or is an alkali metal, an alkaline earth metal or an ammonium ion; or is the group --[CHR₆ (CH₂)_(n4) ]--COOR₇ ; R₆, R₂₀, R₂₁, R₂₆, R₂₈, R₃₂, R₃₄, R₃₉, R₄₀, R₄₆, R₄₇, R₄₉, R₅₀, R₅₁ and R₅₂ are each independently of the others hydrogen or C₁ -C₄ alkyl; R₇ and R₄₈ are each independently of the other hydrogen, C₁ -C₆ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ alkoxy-C₂ -C₈ alkyl, C₁ -C₈ alkylthio-C₁ -C₈ alkyl or C₃ -C₇ cycloalkyl; R₈ is hydrogen or C₁ -C₄ alkyl; R₄₄ and R₄₅ are each independently of the other hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or C₁ -C₄ alkoxy-C₁ -C₄ alkyl; R₉ and R₁₀ are each independently of the other C₁ -C₄ alkyl, C₂ -C₄ haloalkyl or C₂ -C₈ alkoxyalkyl; or R₉ and R₁₀ together are an ethano-, a propano- or a cyclohexane-1,2-diyl bridge, those groups either being unsubstituted or being substituted by one or two radicals selected from the group C₁ -C₄ alkyl, C₁ -C₄ haloalkyl and C₁ -C₄ hydroxyalkyl; R₁₁ is hydrogen, C₁ -C₅ alkyl or C₃ -C₇ alkenyl; R₁₂ is C₁ -C₈ alkyl; R₁₃ is hydrogen, C₁ -C₅ alkyl, benzyl, C₁ -C₄ haloalkyl, C₃ -C₈ alkenyl or C₃ -C₈ halkynyl; R₁₄ is C₁ -C₆ alkyl, C₁ -C₅ haloalkyl or di-C₁ -C₄ alkylamino; R₁₅ is hydrogen, fluorine, chlorine, bromine, C₁ -C₄ alkyl or trifluoromethyl; R₁₆ is chlorine, --X₅ --R₁₇, amino, C₁ -C₄ alkylamino, di-C₁ -C₄ alkylamino, C₂ -C₄ haloalkylamino, di-C₂ -C₄ haloalkylamino, C₁ -C₄ alkoxyalkylamino, di-C₁ C₄ alkoxyalkylamino, C₃ -C₄ alkenylamino, diallylamino, -N-pyrrolidino, -N-piperidino,-N-morpholino, -N-thiomorpholino, -N-piperazino, or the group --O--N═C(CH₃)--CH₃, --O--CH₂ --CH₂ --O--N═C(CH₃)--CH₃ or --N(OR₄₆)--R₆ ; R₁₇ is hydrogen, C₁ -C₁₀ alkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₂ -C₈ haloalkyl, C₁ -C₁₀ alkyl-thio-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, cyano-C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ haloalkenyl, C₃ -C₈ alkynyl, C₃ -C₇ cycloalkyl, C₃ -C₇ cycloalkyl-C₁ -C₄ alkyl, halo-C₃ -C₇ cycloalkyl, or benzyl that is unsubstituted or is substituted at the phenyl ring by one to three identical or different substituents selected from halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy and C₁ -C₄ alkoxy; or is an alkali metal, an alkaline earth metal or an ammonium ion, or is the group --[CHR₄₇ --(CH₂)_(m) ]--COOR₄₈ or --[CHR₄₉ --(CH₂)_(t) --Si(R₁₈)₃ ]; m is 0, 1, 2, 3 or 4; t is 0, 1, 2, 3 or 4; R₁₈ is C₁ -C₄ alkyl; R₁₉ is hydrogen, C₁ -C₆ alkyl, C₂ -C₄ alkenyl or C₂ -C₆ alkynyl; halo-substituted C₁ -C₆ alkyl, C₂ -C₄ alkenyl or C₃ -C₆ alkynyl; C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkoxy-C₁ -C₂ alkoxy-C₁ -C₂ alkyl, 1-phenylpropen-3-yl, C₁ -C₆ alkyl substituted by cyano or by C₃ -C₆ cycloalkyl; carboxy-C₁ -C₄ alkyl, C₁ -C₆ alkoxycarbonyl-C₁ -C₄ alkyl, C₂ - C₆ haloalkoxycarbonyl-C₁ -C₄ alkyl, C₁ -C₄ alkoxy-C₁ -C₂ alkoxycarbonyl-C₁ -C₄ alkyl, C₁ -C₆ alkoxycarbonyl-C₁ -C₂ alkoxycarbonyl-C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl-C₁ -C₂ alkoxycarbonyl-C₁ -C₄ alkyl, C₁ -C₅ alkylaminocarbonyl-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, di-C₁ -C₅ alkylaminocarbonyl-C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, benzyl or halo-substituted benzyl, C₁ -C₄ alkylsulfonyl, C₃ -C₆ alkenyloxy-C₁ -C₄ alkyl, C₁ -C₄ alkoxycarbonyl, C₁ -C₈ alkylcarbonyl, ##STR1025## ##STR1026## C₁ -C₄ alkylthiocarbonyl-C₁ -C₄ alkyl, or the group --[CHR₄₇ -(CH₂)_(m) ]COX₆ --CHR₄₇ --(CH₂)_(m) --COOR₄₈ ; R₂₅, R₂₉, R₃₁, R₃₅ and R36 are each independently of the others hydrogen, C₁ -C₄ alkyl, C₁ -C₆ haloalkyl, C₃ -C₈ alkenyl, C₃ -C₈ haloalkenyl, C₃ -C₈ alkynyl, C₁ -C₄ alkoxy-C₁ C₈ alkyl, cyano-C₁ -C₄ alkyl, C₁ -C₈ alkoxycarbonyl-C₁ -C₄ alkyl, C₃ -C₇ cycloalkyl, C₃ -C₇ cycloalkyl-C₁ -C₄ alkyl, benzyl, C₁ -C₄ alkyl substituted by -N-morpholino, -N-thiomorpholino or by -N-piperazino, di-C₁ -C₄ alkylamino-C₁ C₄ alkyl, C₁ C₄ alkylaminocarbonyl-C₁ -C₄ alkyl, di-C₁ -C₄ alkylaminocarbonyl-C₁ C₄ alkyl, C₁ -C₄ alkoxycarbonyl or C₁ -C₄ alkylcarbonyl; X₁, X₂, X₃, X₄, X₅ and X₆ are each independently of the others oxygen or sulfur, n₁, n₂, n₃ and n₄ are each independently of the others 0, 1, 2, 3 or 4; with the provisos that at least one of R₁, R₂ and A is different from hydrogen; and that when R₅₃ is hydrogen, R₅₄ is different frown C₁ -C₄ alkyl; or a salt or a stereoisomer thereof.
 2. A compound according to claim 1 wherein Z is oxygen.
 3. A compound according to claim 1 of formula Ia ##STR1027## wherein Z, A, R₁, R₂, R₅₃ and R₅₄ are as defined in claim
 1. 4. A compound according to claim 3 wherein A is ##STR1028##
 5. A compound according to claim 4 wherein X₃ is sulfur and R₄ is C₁ -C₆ alkyl substituted by C₁ -C₆ alkoxycarbonyl.
 6. A compound according to claim 3 wherein R₁ and R₂ are halogen.
 7. A compound according to claim 3 wherein R₁ is fluorine and R₂ is chlorine.
 8. A compound according to claim 1 of formula Ib ##STR1029## wherein Z, R₁₉, R₂₂, X₁, R₅₀, R₅₃, R₅₄ and n₁ are as defined in claim
 1. 9. A compound according to claim 8 whereinR₁₉ is C₁ -C₄ alkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -haloalkenyl, C₃ -C₆ alkynyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, cyano-C₁ -C₄ alkyl, C₁ -C₆ alkoxycarbonyl-C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl, C₃ -C₆ cycloalkyl-C₁ -C₄ alkyl, benzyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, C₁ -C₄ alkylaminocarbonyl-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-carbonyl-C₁ -C₄ alkyl, C₁ -C₄ alkoxycarbonyl or C₁ -C₄ alkylcarbonyl.
 10. A compound according to claim 9 whereinZ is oxygen; R₁₉ is C₁ -C₃ alkyl, C₁ C₃ alkoxycarbonyl-C₁ - or -C₂ -alkyl or C₃ - or C₄ -alkynyl; R₂₂ is hydrogen or fluorine; R₅₀ is hydrogen; and n₁ is 0 or
 1. 11. A compound according to claim 1 wherein R₅₃ and R₅₄ are C₁ -C₄ alkyl.
 12. A compound according to claim 11 wherein R₅₃ and R₅₄ are each independently of the other methyl or ethyl.
 13. A compound according to claim 1 wherein R₅₃ and R₅₄, together with the carbon atom to which they are bonded, form an unsubstituted 3- or 5-membered saturated ring.
 14. A compound according to claim 1 wherein R₅₃ is hydrogen; and R₅₄ is C₁ -C₃ alkoxy, C₃ -C₅ alkenyloxy, C₃ -C₅ alkynyloxy or C₁ -C₃ haloalkoxy.
 15. A compound according to claim 14 wherein R₅₄ is C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy.
 16. A compound according to claim 15 wherein R₅₄ is methoxy, isopropoxy or difluoromethoxy.
 17. A compound according to claim 1 selected from the group consisting of:8-(4-chloro-2-fluoro-5-isopropoxy-phenylimino)-3,3-dimethyl-7-thia-1,5-diazabicyclo[3.3.0]octan-6-one; 8-(4-chloro-2-fluoro-5-isopropoxy-phenylimino)-3-methoxy-7-thia-1,5-diazabicyclo-[3.3.0]octan-6-one; 8-(4-chloro-2-fluoro-5-isopropoxy-phenylimino)-3-difluoromethoxy-7-thia-1,5-diazabicyclo[3.3.0octan-6-one; and 8-(4-chloro-2-fluoro-5-isopropoxy-phenylimino)-3,3-ethanediyl-7-thia-1,5-diazabicyclo-[3.3.0]octan-6-one.
 18. A herbicidal and plant-growth-inhibiting composition which comprises a compound of formula I or a salt thereof according to claim 1 in an agriculturally-suitable carrier.
 19. A composition according to claim 18 which comprises from 0.1 to 95 percent by weight of a compound of formula I according to claim 1 in an agriculturally-suiatable carrier.
 20. A method of controlling undesired plant growth, which method comprises treating the crop plants to be protected against weeds and treating the weeds and grasses with a compound of formula I according to claim 1 or with a composition comprising such a compound in an agriculturally-suitable carrier.
 21. A method according to claim 20 which comprises applying a compound of formula I in an amount of from 0.001 to 2 kg per hectare in an agriculturally-suitable carrier.
 22. A method according to claim 20 for the selective pre- or post-emergence control of weeds and grasses in crops of useful plants.
 23. A method of inhibiting plant growth, which method comprises applying to the plants or to the locus thereof an effective amount of a compound of formula I according to claim 1 or of a composition comprising such a compound in an agriculturally-suitable carrier. 